Thumbnail - Startseite...ContentS vii4.3.6 temperature effects on Kinetics, 87 4.3.7 Substituent effects on Kinetics, 90 4.4 Representative Mechanisms, 95 4.4.1 Reactions in Basic

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IntermedIate OrganIc chemIstry


Third Edition

ann m FabIrkIewIczDepartment of Chemistry Randolph College Lynchburg Virginia

JOhn c stOwellDepartment of Chemistry University of New Orleans New Orleans Louisiana

Copyright copy 2016 by John Wiley amp Sons Inc All rights reserved

Published by John Wiley amp Sons Inc Hoboken New JerseyPublished simultaneously in Canada

No part of this publication may be reproduced stored in a retrieval system or transmitted in any form or by any means electronic mechanical photocopying recording scanning or otherwise except as permitted under Section 107 or 108 of the 1976 United States Copyright Act without either the prior written permission of the Publisher or authorization through payment of the appropriate per‐copy fee to the Copyright Clearance Center Inc 222 Rosewood Drive Danvers MA 01923 (978) 750‐8400 fax (978) 750‐4470 or on the web at wwwcopyrightcom Requests to the Publisher for permission should be addressed to the Permissions Department John Wiley amp Sons Inc 111 River Street Hoboken NJ 07030 (201) 748‐6011 fax (201) 748‐6008 or online at httpwwwwileycomgopermissions

Limit of LiabilityDisclaimer of Warranty While the publisher and author have used their best efforts in preparing this book they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose No warranty may be created or extended by sales representatives or written sales materials The advice and strategies contained herein may not be suitable for your situation You should consult with a professional where appropriate Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages including but not limited to special incidental consequential or other damages

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Library of Congress Cataloging‐in‐Publication Data

Fabirkiewicz Ann M 1960ndash Intermediate organic chemistry Ann M Fabirkiewicz Department of Chemistry Randolph College Lynchburg Virginia John C Stowell Department of Chemistry University of New Orleans New Orleans Louisiana ndash Third edition pages cm Includes bibliographical references and index ISBN 978-1-118-30881-3 (cloth) ndash ISBN (invalid) 978-1-118-66227-4 (pdf) ndash ISBN 978-1-118-66220-5 (epub)1 Chemistry OrganicndashTextbooks I Stowell John C (John Charles) 1938ndash1996 II Title QD2512S75 2016 547ndashdc23 2015010086

Printed in the United States of America

10 9 8 7 6 5 4 3 2 1

1 2016

Contents

Preface to the third edition xi

Preface to the second edition xiii

Preface to the First edition xv

1 Reading nomenclature 1

11 Acyclic Polyfunctional Molecules 212 Monocyclic Aliphatic Compounds 313 Bridged Polycyclic Structures 414 Fused Polycyclic Compounds 615 Spiro Compounds 1016 Monocyclic Heterocyclic Compounds 1217 Fused‐Ring Heterocyclic Compounds 1418 Bridged and Spiro Heterocyclic Compounds 19Resources 20Problems 21References 22

vi ContentS

2 Accessing Chemical Information 25

21 Databases 2522 Chemical Literature 2623 Synthetic Procedures 2924 Health and Safety Information 30Problems 32References 33

3 stereochemistry 35

31 Representations 3532 Vocabulary 3733 Property Differences Among Stereoisomers 4034 Resolution of enantiomers 4435 enantioselective Synthesis 4736 Reactions at a Stereogenic Atom 49

361 Racemization 49362 epimerization 50363 Inversion 51364 Retention 51365 transfer 52

37 Relative and Absolute Configuration 5338 topism 56Resources 59Problems 60References 65

4 Mechanisms and Predictions 69

41 Reaction Coordinate Diagrams and Mechanisms 6942 the Hammond Postulate 7143 Methods for Determining Mechanisms 72

431 Identification of Products and Intermediates 72432 Isotope tracing 73433 Stereochemical Determination 74434 Concentration Dependence of Kinetics 75435 Isotope effects in Kinetics 85

ContentS vii

436 temperature effects on Kinetics 87437 Substituent effects on Kinetics 90

44 Representative Mechanisms 95441 Reactions in Basic Solution 96442 Reactions in Acidic Solution 100443 Free‐Radical Reactions 103444 Molecular Rearrangements 106

Resources 108Problems 109References 120

5 electron Delocalization Aromatic Character and Pericyclic Reactions 123

51 Molecular orbitals 12452 Aromatic Character 13053 Pericyclic Reactions 135

531 Cycloaddition Reactions 137532 electrocyclic Reactions 142533 Sigmatropic Reactions 147


6 Functional Group transformations 163

61 Carboxylic Acids and Related Derivatives 164611 Carboxylic Acids 164612 Carboxylic esters 166613 Carboxylic Amides 168614 Carboxylic Acid Halides 168615 Carboxylic Anhydrides 169616 nitriles 169617 ortho esters 170

62 Aldehydes Ketones and Derivatives 171621 Aldehydes 171622 Ketones 174623 Imines and enamines 175

viii ContentS

624 Acetals 175625 Vinyl ethers 177

63 Alcohols 17964 ethers 17965 Alkyl Halides 181

651 Alkyl Chlorides and Alkyl Bromides 182652 Alkyl Iodides 184653 Alkyl Fluorides 184

66 Amines 18567 Isocyanates 18768 Alkenes 18769 Reductive Removal of Functionality 190Resources 191Problems 191References 198

7 CarbonndashCarbon Bond Formation 205

71 CarbonndashCarbon Single Bond Formation 206711 Reactions in Basic Solution 206712 Reactions in Acidic Solution 214713 organometallic Coupling Reactions 217

72 CarbonndashCarbon Double‐Bond Formation 21873 Multibond Processes 222Resources 224Problems 224References 230

8 Planning Multistep syntheses 235

81 Retrosynthetic Analysis 23582 Disconnection at a Functional Group

or Branch Point 23683 Cooperation for Difunctionality 24484 Ring Closure 25085 Acetylide Alkylation and Addition 25386 the DielsndashAlder Reaction 25587 the Claisen Rearrangement 25988 Synthetic Strategies 26389 Final note 265

ContentS ix


9 Physical Influences on Reactions 277

91 Unimolecular Reactions 27892 Homogenous two‐Component Reactions 27993 temperature effects 28094 Pressure effects 28195 Solvent effects 28296 Biphasic Reactions 283

961 Phase transfer Catalysis 283962 Increasing Solubility 286963 Increasing Surface Area 287964 Ultrasound 287

97 Reactions on Chemical Supports 28898 Using Unfavorable equilibria 29199 Green Chemistry 293Resources 294Problems 294References 295

10 survey of organic spectroscopy 299

101 electromagnetic Radiation 299102 Ultraviolet Spectroscopy 300

1021 origin of the Signals 3001022 Interpretation 3021023 Visible Spectroscopy 302

103 Infrared Spectroscopy 3031031 origin of the Signals 3041032 Interpretation 304

104 Mass Spectrometry 3051041 origin of the Signals 3061042 Interpretation 307

105 nMR Spectroscopy 3091051 origin of the Signals 3091052 Interpretation of Proton nMR Spectra 311

x ContentS

106 Carbon nMR Spectra 3231061 General Characteristics 3231062 Interpretation of 13C nMR Spectra 325

107 Correlation of 1H and 13C nMR Spectra 327Resources 329Problems 329References 333

Appendix A 337

Appendix B 341

Index 347

Preface to the third edition

When I read the first edition of Stowellrsquos Intermediate Organic Chemistry I knew I had found an ideal text for a one‐semester advanced organic chemistry course The text was manageable in one semester and the exten-sive references into the primary literature served as an introduction for students interested in pursuing organic chemistry in greater depth and made the text a useful reference beyond the scope of the course

In this revision I tried to stay true to the features that attracted me to the text initially well described in Professor Stowellrsquos preface to the second edition The organization of the book remains much the same The chapter on mechanisms has been moved to early pages of the book as has been the chapter on pericyclic reactions My inclination is to teach mechanisms early as a foundation for the study of reactions but all the chapters have been written with the intent that they can be introduced to the student in any order As much as possible open source materials are cited allowing students ready access to the original literature but at the same time the early work on a topic is found in older literature and that historical value is recognized The second chapter has been completely rewritten to focus on internet accessible resources The last chapter has also been completely rewritten to focus on a survey of organic spectroscopy

I have tried to make this text as error free as possible knowing the frustration of a missing or mistaken reference or a bond misplaced in a

xii PrefAce To The ThIrd edITIon

chemical structure I welcome input from readers of this text Please contact me directly at afabrandolphcollegeedu

I want to thank my husband Steve for his patience and support during the preparation of this manuscript My son Adam is a source of support and insight My mom is an inspiration My colleague Abraham Yousef at Sweet Briar college was helpful in obtaining figures 106 and 1014 Jonathan rose and the team at Wiley have been responsive to all my ques-tions and their assistance is invaluable The support of my family and colleagues has made this work possible

Lynchburg Virginia Ann M fabirkiewiczApril 2015

Preface to the Second edition

consider the typical student who having finished the two‐semester introductory course in organic chemistry and then picking up an issue of the Journal of Organic Chemistry finds the real world of the practicing chemist to be mostly out of reach requiring a higher level of understanding This text is intended to bridge that gap and equip a student to delve into new material

There are two things to know while studying organic chemistry one is the actual chemistry that is the behavior of compounds of carbon in various circumstances The other is the edifice of theory vocabulary and sym-bolism that has been erected to organize the facts In first‐year texts there is an emphasis on the latter with little connection to the actual observables Thus students are able to answer subtle questions about reactions without knowing quite how the information is obtained chemistry is anchored in observations of specific cases which can be obscured by the abstractions for this reason this text includes specific cases with more details and literature references to illustrate the general principles Understanding these cases is an exercise to ensure the understanding of those general principles in a concrete way

Many of the problems begin with raw data and require multistep thinking Therefore the student must solve a problem from the beginning rather than from a half‐finished setup and more thought and puzzling is necessary

xiv PrefAce To The Second edITIon

This book is selective out of the endless possibilities of reactions a specific limited criteria were chosen and the chapters are consistent within that criteria Likewise the problems in the chapters were chosen selec-tively that fulfils the criteria as well as reactions from the introductory organic courses These selections were made based on the number of times they appeared in many current journal articles review references are given to aid a student who wishes to go further with these topics Subjects that are generally well covered in introductory courses are either omitted or briefly reviewed here Advanced topics are treated to a functional level but not exhaustively

for those familiar with the first edition you will find that major changes have been made in all the chapters new examples have been added and many others have been replaced with better ones The explanations have been elaborated and illuminated with more detail The same 10 chapters have been retained but new sections have been added and material reorganized Substantial update has been done including stereochemical terminology and the nMr chapter has been reframed in terms of pulsed high‐field spec-trometers About twice as many exercise problems are available at the end of most chapters

New Orleans Louisiana John c StowellOctober 1993

Preface to the firSt edition

consider a typical student who has finished a two-semester introductory course in organic chemistry and then picks up an issue of the Journal of Organic Chemistry he or she finds the real world of the practicing organic chemist to be mostly out of reach on a different level of understanding This text is intended to bridge that gap and equip a student to delve into new material

There are two things to know while studying organic chemistry one is the actual chemistry that is the behavior of compounds of carbon in var-ious circumstances The other is the edifice of theory vocabulary and symbolism that has been erected to organize the facts In first-year texts there is an emphasis on the latter with little connection to the actual observ-ables Thus students are able to answer subtle questions about reactions without knowing quite how the information is obtained chemistry is anchored in observations of specific cases which can then be obscured by the abstractions for this reason this text includes specific cases with more details and literature references to illustrate the general principles Understanding these cases is also an exercise to ensure the understanding of those principles in a concrete way

This book is by necessity a selection Subjects that are generally well covered in introductory texts are omitted or briefly reviewed here Advanced topics are treated to a functional level but not exhaustively Specifically the subjects are those necessary for understanding and

xvi PrefAce To The fIrST edITIon

searching the literature and some topics that are the elements of many current journal articles The outcome is a selected sampling on a scale with latitude for creative lecturers to amplify with their own selections Advanced texts give much attention to classical work that led to modern understanding This text with all due respect to the originators does not cover that familiar ground but again covers current examples grounded in those classical ideas with modern interpretation

There is a modicum of arbitrariness in the selections and considering this text as a new experiment the author would welcome suggestions for substitutions and improvements

New Orleans Louisiana John c StowellNovember 1987

Intermediate Organic Chemistry Third Edition Ann M Fabirkiewicz and John C Stowell copy 2016 John Wiley amp Sons Inc Published 2016 by John Wiley amp Sons Inc

1Reading nomenclatuRe

Organic chemistry is understood in terms of molecular structures as represented pictorially Cataloging writing and speaking about these structures require a nomenclature system the basics of which you have studied in your introductory course To go further with the subject you must begin reading journals and this requires understanding of the nomenclature of complex molecules This chapter presents a selection of compounds to illustrate the translation of names to structural representa-tions The more difficult task of naming complex structures is not covered here because each personrsquos needs will be specialized and can be found in nomenclature guides [1ndash5] Most of the nomenclature rules are used to eliminate alternative names and arrive at a unique (or nearly so) name for a particular structure thus when beginning with names you will need to know only a small selection of the rules in order to simply read the names and provide a structure Although the subject of nomenclature is vast these selections will enable you to understand many names in current journals

2 ReAding nOMenClATuRe

11 acYclic PolYFunctional moleculeS

Methyl (3S4S)‐4‐hydroxy‐3‐(phenylmethoxy)hex‐5‐enoate

The space after methyl and the ldquoaterdquo ending tells you this is a methyl ester The acid from which the ester derives is a six‐carbon chain with a double bond between carbons 5 and 6 There is an alcohol function on carbon 4 There is a methoxy group on carbon 3 and a phenyl group on the carbon of the methoxy group Carbons 3 and 4 are stereogenic atoms each with S configuration as designated

3‐(S)‐trans‐1‐iodo‐1‐octen‐3‐ol methoxyisopropyl ether

This is an example of a derivative name that is the first word is the complete name of an alcohol and the other two words describe a derivati-zation where the alcohol is converted to an ether (ketal) Such a name would be useful in discussing a compound that has the ketal present as a temporary entity for example as a protecting group

ethyl (E3R6R)‐368‐trimethyl‐8‐[(trimethylsilyl)oxy]‐7‐ oxo‐4‐nonenoate

CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS

MOnOCYCliC AliPHATiC COMPOundS 3

This is the ethyl ester of a nine‐carbon unsaturated acid with substituents The oxo indicates that there is a keto function on carbon 7 Be careful to distin-guish this from the prefix oxa‐ which has a different meaning see Section 16 The asterisks indicate that the configuration designation is not absolute but rather represents that stereoisomer andor the enantiomer thereof Thus this name represents the RR andor the SS isomers but not RS or SR This desig-nation excludes diastereomers and is a common way to indicate a racemate

12 monocYclic aliPHatic comPoundS

(1S3R)‐22‐dimethyl‐3‐(3‐oxobutyl)cyclopropanecarboxylic acid

The ring is placed in the plane of the paper numbering of the ring starts at the location of the highest priority substitution the carboxylic acid in this case The butyl substituent on the third carbon of the ring has a keto function on the third carbon of the butyl chain

[2S‐(1E2α3α5α)]mdash[3‐(Acetyloxy)‐2‐hydroxy‐2‐methyl‐5‐(methylethenyl) cyclohexylidene]acetic acid ethyl ester

The ylidene indicates that the cyclohexyl is attached to the acetic acid by a double bond and the ethyl ester is indicated at the end for simplicity The double‐bonded ring atom is carbon 1 and the substituents on the ring are placed on the ring according to their locant numbers The E indicates

O

HO

O

O

OOH

O

O


the geometry of the double bond All the α substituents reside on one face of the ring cis to each other Any β substituents would reside on the opposite face of the ring trans to the α substituents Where two substituents are on the same ring atom as on carbon 2 in this case the greek letter indicates the position of the higher‐priority substituent Here the hydroxy acetyloxy and methylethenyl are all cis to each other on the ring

13 BRidged PolYcYclic StRuctuReS

The nomenclature of bridged polycyclic systems requires additional specifi-cations A bicyclic system would require two bond breakings to open all the rings a tricyclic system three and so on Rather than viewing this as rings certain carbons are designated as bridgeheads from which the bridges branch and recombine in the system below the first bridgehead is designated as carbon 1 and the system is numbered around the largest bridge to the second bridgehead carbon 5 numbering continues around the medium bridge then the smallest bridge as shown The compound is named bicyclo[321]octane

17

6

5

8

4

2

3

All bicyclo compounds require three numbers in brackets tricyclo require four and so on and these numbers indicate the number of carbons in the bridges and are used to locate substituents heteroatoms and unsat-uration The name of the parent alkane includes the total number of atoms in the bridges and bridgeheads (excluding substituents) and is given after the brackets The use of prefixes exo endo syn and anti to indicate ste-reochemical choices is demonstrated generally as shown below

synanti

exo

endo endo

exo X

synanti

BRidged POlYCYCliC STRuCTuReS 5

in tricyclic compounds the relative stereochemistry among the four bridgeheads requires designation look at the largest possible ring in the molecule and consider the two faces of it if there are no higher‐priority substituents on the primary bridgehead atoms the smallest bridge (but not a zero bridge) defines the α face if the smallest bridge (not zero) at the secondary bridgeheads is on the same face of the large ring as the α defining one it is also designated as α that is the two are cis to each other

51 2

6

1α2β5β6α 1α2α5α6α

if they are trans there will be two αs and two βs as illustrated if there is a zero bridge the position of the bridgehead hydrogens is indicated with greek letters

[1S‐(2‐exo3‐endo7‐exo)]‐7‐(11‐dimethylethyl)‐3‐nitro‐2‐phenylbicyclo [331]nonan‐9‐one

This bicyclo system has bridges with three three and one carbons each indicated by the bracketed numbers separated by periods Carbon 2 carries a phenyl that projects toward the smaller neighboring one‐carbon bridge rather than the larger three‐carbon bridge as indicated by 2‐exo The 11‐dimethylethyl group is also exo This group is commonly called tert‐butyl but this is a Chemical Abstracts name built on linear groups The prefixes exo and endo indicate the stereochemistry

(1α2β5β6α)‐Tricyclo[421025]non‐7‐ene‐34‐dione

O2N

O


O

O12

567

Starting with a pair of bridgeheads draw the four‐ two‐ and one‐carbon bridges The zero bridge then connects carbons 2 and 5 as indicated by the superscripts thus making them bridgeheads also At bridgeheads 1 and 6 the smallest bridge is considered a substituent and given the α designation at both ends At bridgeheads 2 and 5 the βs indicate that the hydrogens are trans to the α bridge

Sometimes a bridgehead substituent will have a higher priority than the smallest bridge thereon The designation for that bridgehead will indicate the position α or β of that higher‐priority substituent rather than the bridge as illustrated in the next example

(1α2β4β5β)‐5‐Hydroxytricyclo[332024]deca‐79‐dien‐6‐one

O

HO

12

4

7

9

10

At bridgehead 1 the smallest bridge carbons 9 and 10 is considered a substituent on the largest ring and designated α The hydrogens at carbons 2 and 4 are trans to it and marked β The OH group on carbon 5 is a higher‐priority substituent than the C‐9 to C‐10 bridge and is trans to the bridge thus it is labeled β

14 FuSed PolYcYclic comPoundS

Fused‐ring compounds have a pair or pairs of adjacent carbon atoms common to two rings Over 35 carbocyclic examples have trivial names some of which need to be memorized as building blocks for names of more complex examples The names end with ene indicating a maximum

FuSed POlYCYCliC COMPOundS 7

number of alternating double bonds A selection is illustrated in Table 11 showing one resonance form for each Others can be found online [6]

Fusing more rings onto one of these basic systems may give another one with a trivial name if not a name including the two rings or ring systems with bracketed locants is used as in the following example

712‐dimethylbenz[a]anthracene

1

4

5

68

11

a

b

cdefgh

i

j k l m n

taBle 11 trivial names of Some Fused Polycyclic Hydrocarbons

12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5

naphthalene Phenanthrenea Anthracenea

1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89

Azulene indene Fluorene

1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12

Pyrene Triphenylene Chrysenea exceptions to systematic numbering


Since a side of the anthracene is shared the sides are labeled a b c and so on where carbons numbered 1 and 2 constitute side a and 2 and 3 constitute side b continuing in order for all sides The earliest letter of the anthracene is used to indicate the side fused and the ring fused to it appears first The ldquoordquo ending of benzo is deleted here because it would be followed by a vowel

The final combination is then renumbered to locate substituents or sites of reduced unsaturation To renumber first orient the system so that a maximum number of fused rings are in a horizontal row if there are two or more choices place a maximum number of rings to the upper right Then number clockwise starting with the carbon not involved in fusion in the most counterclockwise position in the uppermostndashfarthest right ring See the numbering in the systems with trivial names above Atoms at the fusion sites which could carry a substituent only if they were not π‐bonded are given the number of the previous position with an a b c and so on Where there is a choice the numbers of the fusion carbons are minimized too for example 4b lt 5a

1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect

1H‐Benz[cd]azulene

a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene

First letter the sides of azulene The benzo ring is fused to both the c and d faces as indicated in the brackets now reorient the system for numbering The choice of which two rings go on the horizontal axis and


which one is in the upper position is determined by which orientation gives the smallest number to the first fusion atommdashin this case 2a instead of 3a or 4a in molecules where one carbon remains without a double‐bonding partner it is denoted by H This is called indicated hydrogen and is used even when an atom other than hydrogen is actually on that carbon in the molecule of interest

trans‐1234‐Tetrahydrobenzo[c]phenanthrene‐34‐diol diacetate

O

O

O

O1

2

5

12

7

andor enantiomer

The sides of phenanthrene are lettered the carbons numbered 3 and 4 are the c side As in several systems phenanthrene is numbered in an exceptional way A benzene ring is fused to the c side and a new systematic numbering is made Carbons 1ndash4 have hydrogens added to saturate two double bonds and then carbons 3 and 4 have hydroxy groups substituted for hydrogens in a trans arrangement Finally the compound is named as the acetate ester at both alcohol sites

613‐dihydro‐5H‐indeno[21‐a]anthracene‐712‐diol

OH

OH

1 2

13

58

11


The fusion of this ring system is given in the brackets The bracketed a precedes anthracene indicating that the sides of anthracene will be lettered and the bracketed 21 follows the indene thus the indene numbering indi-cated in Table 11 will be used to give the point of fusion The order of the numbers indicates the direction of the fusion thus the carbons of indene are fused in order 2 then 1 to the a side of anthracene with the number 1 carbon of anthracene constituting the number 2 carbon of indene and the number 2 carbon of anthracene the number 1 carbon of indene The united system is then renumbered according to the rules and the substituents added hydrogen and indicated hydrogen placed accordingly The indicated hydrogen is assigned the lowest‐numbered atom not involved in double bonding

The other direction of fusion is in 1H‐indeno[12‐a]anthracene

1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c

Correct incorrect4a 5a 7a 8a 12a 12b 12c 13a 4a 5a 7a 8a 12a 13a 13b 13c

note that here a different orientation is used because it gives the lower fusion numbers

15 SPiRo comPoundS

in spiro compounds a single atom is common to two rings There are two kinds of nomenclature for these Where there are no fused rings present the carbons of both rings are counted in one series as in the bicyclic nomen-clature and the hydrocarbon name includes the carbons of both rings as in the following example

SPiRO COMPOundS 11

4‐Oxospiro[26]nonane‐1‐carboxylic acid methyl ester

O

OCH3

O

1

2

3

5

9

Of the nine carbons one is the spiro atom two join round to make a three‐membered ring and six finish a seven‐membered ring as indicated by the bracketed numbers The locant numbers begin in the smaller ring at an atom adjacent to the spiro one continue around the smaller ring including the spiro atom and proceed around the larger ring

When ring fusion is also present the two ring systems that share the spiro atom are given in brackets with splicing locants as shown in the following example

3prime4prime‐dihydro‐5prime8prime‐dimethylspiro[cyclopentane‐12prime(1primeH)‐naphthalene]

1

21

5

2

4

8

Two separate numbering systems are used The unprimed number belongs to the ring nearest it in the brackets the cyclopentane while the primed numbers belong to their nearer neighbor in the brackets naphtha-lene The locant numbering in the fused system follows the usual pattern (Section 14) and is identified with primes The ‐12prime indicates that the shared atom is number 1 of the cyclopentane ring and number 2prime of the naphthalene The spiro linkage requires another naphthalene ring atom to be excluded from double bonding in this case the 1prime as determined by the indicated hydrogen 1primeH


16 monocYclic HeteRocYclic comPoundS

Systematic and trivial names are both commonly in use for heterocyclic compounds The systematic names consist of one or more prefixes from Table 12 with multipliers where needed designating the heteroatoms followed by a suffix from Table 13 to give the ring size with an indication of the unsaturation This is preceded by substituents Thus oxepin is a

taBle 12 Prefixes in order of decreasing Priorityab

Oxygen ox‐Sulfur thi‐Selenium selen‐nitrogen az‐Phosphorus phosph‐ (or phosphor‐ before ‐in or ‐ine)Silicon sil‐Boron bor‐

a From Ref [7]b An ldquoardquo is added after each prefix if followed by a consonant

taBle 13 Suffixes indicating Ring Sizea

Atoms in the Ring

Containing nitrogen Containing no nitrogen

Maximally unsaturated Saturated


3 ‐irine ‐iridine ‐irine ‐irane4 ‐ete ‐etidine ‐ete ‐etane5 ‐ole ‐olidine ‐ole ‐olane6 ‐ine mdashb ‐in ‐ane7 ‐epine mdashb ‐epin ‐epane8 ‐ocine mdashb ‐ocin ‐ocane9 ‐onine mdashb ‐onin ‐onane

10 ‐ecin mdashb ‐ecin ‐ecanegt10c mdash mdash mdash mdash

a From Ref [7]b use the unsaturated name preceded by ldquoperhydrordquoc use the carbocyclic ring name with heteroatom replacement prefixes oxa‐ thia‐ and so forth



Third Edition












10 9 8 7 6 5 4 3 2 1

1 2016

Contents






vi ContentS










ContentS vii











viii ContentS











ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring








Third Edition












10 9 8 7 6 5 4 3 2 1

1 2016

Contents






vi ContentS










ContentS vii











viii ContentS











ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring
















10 9 8 7 6 5 4 3 2 1

1 2016

Contents






vi ContentS










ContentS vii











viii ContentS











ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring







Contents






vi ContentS










ContentS vii











viii ContentS











ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring







vi ContentS










ContentS vii











viii ContentS











ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring







ContentS vii











viii ContentS











ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring







viii ContentS











ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring







ContentS ix












x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring







x ContentS



Appendix A 337

Appendix B 341

Index 347



































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring









































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring





































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring

































CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring





























CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring

























CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring





















CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring

















CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring














CH3O

O

OH

O

I

O OCH3

O

O O

OSiMe3O

O O

OSiMe3+

RR SS








O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring














O

HO

O

O

OOH

O

O





17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring











17

6

5

8

4

2

3


synanti

exo

endo endo

exo X

synanti



51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring









51 2

6






O2N

O


O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring








O

O12

567




O

HO

12

4

7

9

10








1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring











1

4

5

68

11

a

b

cdefgh

i

j k l m n


12

3

45

6

7

81

2

3456

7

8

9 10

19

10

2

34

8

7

6

5


1

2

34

5

6

7 81

2

34

5

6

7 1

2

3456

7

89


1

2

3

4

567

8

9

1011

12

10

98

7

6

5

4

3

2

11

2

3

45

67

8

9

1011

12





1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring










1

44a4b

5

89

9a8a

54a

1

45a

9a 9b9

Correct incorrect


a

bcde

f

gh i j

5

9

1 2

2a

5a

9a

Azulene





O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring










O

O

O

O1

2

5

12

7

andor enantiomer



OH

OH

1 2

13

58

11




1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring










1

2

4a

5a

7a8a

12a12c

1

2

4a

5a

8a 7a

12a 13a

13c



15 SPiRo comPoundS


SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring







SPiRO COMPOundS 11


O

OCH3

O

1

2

3

5

9




1

21

5

2

4

8









Atoms in the Ring














Atoms in the Ring







Documents

Thumbnail - Startseite...ContentS vii4.3.6 temperature effects on Kinetics, 87 4.3.7 Substituent effects on Kinetics, 90 4.4 Representative Mechanisms, 95 4.4.1 Reactions in Basic