Gaylord Chemical Company, L.L.C. (GCC) is the world’s leading provider of Dimethyl Sulfoxide (DMSO) solutions. Beginning in the early 1960’s ,GCC has been dedicated to the development of new uses for DMSO. In order to meet customer-specific needs, GCC has pioneered the devel-opment of multiple grades of DMSO, including DMSO USP. Gaylord Chemical’s solutions-based approach has contributed to the development and growth of industries including pharmaceuticals, hydrocarbons, electronics, polymers, coatings, agricultural chemicals, and industrial cleaners. Gaylord Chemical’s headquarters are located in Slidell, Louisiana with manufacturing, research, and

development facilities in nearby Bogalusa, Louisiana. GCC remains the only producer of DMSO in the Western Hemisphere.

Oct 2007

Dimethyl Sulfide

Reaction Solvent Guide

TABLE OF CONTENTS Page General Information 3 Chemical Reactions of Dimethyl Sulfide: Cleavage with Hydrogen Sulfide 4 Reaction with Halogens 5 Reaction with Halogenating Agents 5 Reactions of Halogen Derivatives of DMS 6 Oxidation of DMS 8 Reactions with Acylperoxides or Lead Tetraacetate 9 Reaction with Tetracyanoethylene Oxide 9 Alkylation 9 Solvation 11 Formation of Sulfilimines 12 Formation of Sulfonium Polymers and Resins 13 Reaction with Sulfur 15 Reaction with Dehydrobenzene (Benzyne) 15 Borane-Dimethyl Sulfide Adduct 15 Ozonolysis 16 Sulfur Ylide Chemistry 16 Allylic Chlorination 16 Conjugate Addition 17 Thioalkylation 17 MTM Ether Protection of Alcohols 18 Glycosylation 18 Bibliography 19

Bulletin # 203B

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3

General Information Dimethyl sulfide (DMS) is a nonpolar, stable, water-white liquid, boiling at 37°C. Although it is immiscible with water, it is miscible with most common organic solvents. It is capable of dissolving a wide range of both organic and inorganic materials and forms stable complexes with many inorganic compounds. See Gaylord Chemical Company, L.L.C. bulletin 200B for more details on properties of DMS. Small amounts of DMS have been used for many years, with its history dating back to 1840 when it was first synthesized by V. Regnault of Germany. Because of its solvency characteristics, its odor, and its chemical reactivity, dimethyl sulfide has found wide use in the chemical industry and is now available as a bulk organic chemical. Dimethyl sulfide also occurs naturally, and has been identified as an important factor in the flavor and odor characteristics of dairy products, fish, tea, and other food products. Dimethyl sulfide has a distinctive, ethereal odor, and intensifies and enhances other odors. This property has prompted its use in natural gas odorants and as an intensifier in odor masking compounds. Chemically, DMS is an extremely stable molecule and normally undergoes reactions only at the sulfur atom. In some cases, however, the initial reaction product rearranges to produce a final product in which the hydrogen atom on a carbon is replaced by the introduced group. The hydrogen atoms in DMS are quite inert, and resist direct attack even by butyl lithium. They can, however, be attacked by halogens. From the following information, it will be seen that dimethyl sulfide and its derivatives offer new and interesting possibilities in the chemical and related industries.

Chemical Reactant DMS will undergo several types of reactions and may be used as a source for the following reactive groups:

Additional details concerning these and other reactions are presented in the following section.

Chemical Reactions of Dimethyl Sulfide

4

While DMS is not considered to be a reactive molecule and is known as a stable solvent, it does undergo reactions at the sulfur atom. The presence of unshared electron pairs allows the molecule to form complexes with molecules that are deficient in unshared electrons. In this sense, it is considered to react as a Lewis base. Often the formation of complexes activates the other bonds resulting in cleavage and reaction with other molecules. Replacement of its hydrogen atoms by halogen also leads to greater reactivity. DMS is a potential source of the following groups:

Cleavage with Hydrogen Sulfide 1

This reaction occurs rapidly in the vapor phase over an activated alumina catalyst at 350° - 400° C.

Grouping Name

Methylthiomethyl

Dimethylalkylsulfonium

Methylthio (methylsulfenyl)

Methylsulfinyl

Methylsulfonyl

Dimethylsulfonium ylide

Dimethylsulfilimine

5

The equilibrium constant at 400° C is approximately 1.0. Reaction with Halogens (a) At Low temperature, anhydrous,

These crystalline adducts are known for chlorine, bromine and iodine. The chlorine compound is unstable above -10° C and rearranges to monochlorodimethyl sulfide above that temperature. Hydrolysis of the bromine and chlorine adducts produces dimethyl sulfoxide (DMSO). The adducts may serve as mild halogenating agents and the bromine complex has been used to brominate aniines, amides and olefins. (b) In aqueous suspension

2, 3

DMS has been converted to mesyl chloride by chlorination in water in 50-60% yields. The yield can be increased to above 75% by first chlorinating the sulfide to at least the monochloro stage before introducing water. (c) Chlorination dry at room temperature

4, 5

This reaction in its initial stage is extremely rapid and produces visible light. The monochloro derivative can, however, be prepared by direct chlorination in the vapor phase by introducing an inert diluent such as hydrogen chloride along with the DMS and chlorine to help moderate the vigor of the reaction. After the monochloro derivative has been formed, the reaction with chlorine proceeds smoothly and stepwise until tetrachlorodimethyl sulfide is formed. The hydrogen atoms on one carbon are replaced before attack occurs on the other. Chlorination beyond the tetrachloro derivative leads mainly to cleavage giving carbon tetrachloride, chloromethylsulfenyl chloride and its chlorinated products. Reaction with Halogenating Agents DMS reacts smoothly with reagents such as S2Cl2, SOCl2

6, SO2Cl2

6, and PCl5

7 in stepwise fashion

to produce all the chlorinated derivatives shown above. The sulfur halides can also be used to make the penta- and hexachloro-derivatives. S2Cl2, SOCl2 or PCl5 are preferred for making the

6

monochloro-derivative and SO2Cl is used for the higher ones. PCl5 has been claimed to produce a higher yield of a lighter colored mono-product.

7

The fluoro-derivatives cannot be prepared directly but may be obtained easily by treating the Chloro-derivatives with mercuric fluoride

8 in ether solution or antimony pentafluoride

9. With the tetrachloro-

derivative and antimony pentafluoride, the chlorine atoms on the carbon carrying the 3 chlorines are replaced.

Reactions of Halogen Derivatives of DMS Monochlorodimethyl sulfide is an active alkylating agent for introducing the CH3-S-CH2- group. Chloro, nitro and other substituted phenols have been reacted with monochloro DMS in the presence of Friedel-crafts catalysts to produce substituted alpha (methylthio)cresols.

10

The resulting products from these reactions are reported to be useful as antioxidants, germicides, herbicides and seedicides. Monochioro DMS also reacts with the sodium derivative of dimethyl malonate to give methylmercaptomethyl malonic acid dirnethyl ester. The reaction may proceed further than monoalkylation, and methylene malonic acid dimethyl ester and propane tetracarboxylic acid tetramethyl ester may also be formed.

11

6-diketones and 8-ketocarboxylic acid esters can also be alkylated.12

7

In addition to alkylating phenols, the mono-, di- and trichloro derivatives with Freidel-Crafts catalysts can also alkylate many aromatic hydrocarbons and ethers.

13 The monochloro derivative gives

methylbenzyl sulfides

The dichloro and trichloro derivatives give chloro substituted methylbenzyl sulfide intermediates which can be hydrolyzed to aldehydes and thiol esters of aromatic carboxylic acids in high yields.

The reactions may also be extended to polynuclear aromatics and heterocyclic compounds. Monochloro DMS also undergoes other interesting transformations. It reacts with potassium

8

thiocyanate in petroleum ether solvent to give a good yield of methylthiomethylisothiocyanate, one of the constituents of the volatile oils of cabbages.

14

It reacts readily with thiourea to give the isothiouroniurn salt14

and the salt can be hydrolyzed to methylthiomethyl mercaptan.

15

Other reactions are with carbonyl sulfide or carbon disulfide and a mixture of secondary and tertiary amines to produce methylthiomethyl-N, N-dialkylthiolcarbamates.

The carbamates have been used as cost effective and reliable weed control agents when applied to soil.

The trichloro DMS derivative can be converted to the sulfone by treatment with a suitable oxidizing agent such as chromic oxide. The sulfone then can undergo a very novel reaction with an alkoxy phosphite ester. The reaction involves formation of carbon to carbon bonds resulting in the preparation of novel α, α -dichloro sulfones.

18

(16)

(17)

9

Many of the resulting dichlorosulfones have been useful as fungicides and insecticides. Oxidation of DMS

DMS is oxidized by many reagents such as hydrogen peroxide

19, nitrogen dioxide, nitric acid,

permanganate20

, chromic oxide, chromate ion, hypochlorite, ozone and others.21

The oxidation takes place in stepwise fashion and stops at the sulfoxide stage under anhydrous conditions when nitrogen dioxide, tetroxide or air containing nitrogen oxide as catalyst is used. The other oxidants can be used to yield either the sulfoxide or the sulfone. Reactions with Acylperoxides or Lead Tetraacetate

The same final product results from the use of either lead tetraacetate or acetyl peroxide. The reaction proceeds by forming an acetoxysulfonium acetate which rearranges to the acetoxymethyl sulfide.

Reaction with Tetracyanoethylene Oxide

(24)

10

Dimethyl sulfide reacts readily with tetracyanoethylene oxide to give a precipitate of dimethysulfonium dicyanomethylide leaving carbonyl cyanide in excess DMS solution.

22, 23 The

methylide can be recrystallized from isopropanol and is useful as an ingredient of plastic compositions and fabric coatings to enhance the electrical properties of the plastics. Plastics containing the methylide are claimed to be particularly useful as phosphor binders in electroluminescent lighting panels. Carbonyl cyanide is a useful reagent for reaction with various olefinic compounds. The older method for preparing it was time-consuming and hazardous due to risks of explosion. Alkylation

Alkylation occurs with the usual alkylating agents and is usually run at room temperature. Benzyl chloride or bromide, alkyl benzyl halides, methyl iodide or sulfate and others react to form sulfonium salts. Sulfonium salts are ionic molecules and are generally water soluble. They exhibit surfactant properties in many cases. A particularly interesting sulfonium compound, trimethylsulfonium hydroxide (TMSOH) can be prepared readily from trimethylsulfonium chloride by two methods: (a) metathesis with NaOH in alcohol solution, and (b) ion exchange with a basic ion exchange resin.

TMSOH is a strong organic base. It is labile to heat and may be destroyed by warming. Use may be made of this property where the transient effect of a strong base is desired. By warming, the TMSOH can be converted to volatile products so that it does not appear in the final product. Trimethylsulfonium halide on treatment with very strong bases such as sodium hydride or DMSO anion is converted to dimethysulfonium methylide.

25

11

The dimethylsulfonium methylide is a very reactive intermediate and rapidly adds a methylene group to many unsaturated systems. Reaction with carbonyl functions produces oxiranes, often with yields in excess of 90%.

25

β-propiolactone reacts with DMS in the presence of HCl to give 75-80% reaction according to the following equation.

26

This sulfonium salt is of interest because of possible biological importance in methyl transfer reactions.

Solvation The electron pairs on the sulfur atom in DMS are available to form coordinate bonds with metallic ions.

27, 28 Many of these complexes are stable enough to isolate while others are stable enough only

to make the salt soluble in DMS. The halide and cyanide salts of the transition metals are usually soluble while those of alkali or alkaline earth metals are insoluble. The crystalline complexes contain one or two molecules of DMS.

The normal metal halide salt adducts of a number of metal halides can react with HC1 to give sulfonium salts with hydrogen attached to the DMS sulfur atom.

29 Such salts are stable at low

temperatures but release HCl at higher temperatures.

A number of very interesting and important complexes can be made by reactions of DMS with various boron compounds.

30, 31, 32, 33

DMS reacts with decaborane at room temperature and reduced pressure to give an almost quantitative yield of a white solid adduct.

12

The unique B10H12• 2(CH3)2S compound can be used as the starting point for preparations of other borane compounds. It can be reacted, for example, with liquid ammonia to give the ammonium salt of the B10H10 anion.

It can also react with amines to give the amine of the anion.

The resulting amine complex can be passed through an acidic ion exchange column to convert it to a strongly acidic material.

The decaborane acid is considered to be as strong as sulfuric acid. Formation of Sulfilimines DMS reacts with chloramine-T in ethanol or acetone solution at temperatures of 40° C or less to give an insoluble sulfilimine product.

34

DMS also reacts with the sulfonyl nitrene fragments resulting from the photolysis of sulfonyl azides to give fairly high yields of N-sulfonylsulfilimines.

35

DMS reacts with one mole of chloramine to give only a very low yield of the simplest alkyl sulfilimine hydrochloride, but gives a good yield of a sulfiliminium sulfate when reacted with hydroxylamine sulfonic acid in the presence of sodium methoxide.

36

13

When two moles of chloramine are reacted with DMS or when chloramine is reacted with a preformed sulfilimine, a diimine product is formed.

37

The diimine hydrochloride can be neutralized by treatment with bases and other salts can be made by treatment with appropriate acids. The various diimines are reported to have excellent fungicidal activity and to be useful as rubber vulcanizing agents and polymer stabilizers. Formation of Sulfonium Polymers and Resins A number of methods of preparing sulfonium type ion exchange resins have been discovered. One of the first of the sulfonium resins was developed in Japan by H. Kawabe and M. Yanagita in 1957.

38,

39 This resin containing benzyldimethylsulfonium groups is prepared by chloromethylating bead form

copolymers of styrene and divinylbenzene and then reacting the chloromethyl groups with dimethyl sulfide. The resulting benzyl sulfonium salts are converted to the basic form by treatment with alkali.

14

The sulfonium type resin is reported to be more selective for monovalent ions than quaternary ammonium resins. The selectivity can be somewhat controlled since it appears to increase as the cross-linking in the resin system increases. The resins are reported to be useful in the separation of heavy radioactive metals and for decolorizing sugar solutions. Another way to prepare sulfonium type polymers is to react a vinylbenzyl halide with dimethyl sulfide. The resulting sulfonium monomers can be polymerized by methods conventionally used with free radical catalyzed aqueous systems.

40

15

The resulting polymers are reported to be useful as water soluble cationic thickening agents and slime flocculators. When the sulfonium polymers are mixed with water soluble polycarboxylate resins, the resulting mixture can be added to cellulose webs to increase both the wet and dry strengths of paper made from the cellulose.

41

Reaction with Sulfur In the presence of Friedel-Crafts catalysts such as zinc chloride or boron trifluoride, DMS reacts readily with elemental sulfur to produce polysulfides containing large amounts of chemically bound sulfur. Heating DMS with sulfur alone causes only a minor amount of polysulfide to be found . Friedel-Crafts catalysts permit the reaction of large amounts of sulfur, at low temperatures and short reaction times.

42

The polysulfides are used as vulcanization accelerators and in the compounding of pressure lubricants. They are also reported to be effective fungicides, nematocides and bactericides.

Reaction with Dehydrobenzene (Benzyne) Treatment of o-chlorobromobenzene with butyl lithium forms dehydrobenzene (benzyne). This material reacts with dimethyl sulfide to give a sulfonium intermediate which rearranges to the ylid.

43

The ylid is stabilized by excess butyl lithium and can undergo reactions typical of this very reactive molecule.

O N

O

OH

HO2C

O N

O

OH

HOBH3-DMS, THF, 0C

Borane-Dimethyl Sulfide Adduct The unstable nature and low reactivity toward alkenes of diborane itself has resulted in the develop-ment of numerous more reactive complexes paramount among which are borane-THF and borane-dimethyl sulfide. Among these two the Borane-DMS complex is preferred because of its greater stability. The reduction shown is an intermediate step in the synthesis of SJ-749, a drug in biologi-cal testing in the United States (US 5,760,029, assignee Bristol-Myers-Squibb Corporation).

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Functional groups that are readily reduced by borane-methyl sulfide (BMS) include aldehyde, ke-tone, carboxylic acid, amide, oxime, imine, and nitrile moieties. The carboxylic acid group is re-duced at a faster rate than most groups including non-conjugated alkene. Carboxylic acids can be protected from reduction as trialkylsilyl esters [Kabalka, GW; Bierer, D. Organometallics, 8, 655 (1989)]. Its effectiveness has also been examined for carbonyl compounds. [E. Mincione, J. Org. Chem., 43, 1829 (1978). BMS is one of several effective borane options for asymmetric ketone re-duction using chiral oxazaborolidine catalysts ([Corey, E.J.; Helal, C. J. Angew.Chem. Int. Ed. 1998, 1986). Ozonolysis DMS is the preferred reagent for decomposing ozonide / molozonide intermediates in the oxidative cleavage of alkenes with ozone. The example below shows this reaction in an intermediate to TAK-187, an antifungal agent in clinical trials in the US (JP1995228574, assignee Takeda Pharmaceuti-

Sulfur Ylide Chemistry The sulfur ylide produced when trimethylsulfonium salts are deprotonated are valuable tools for the synthesis of epoxides (Corey, E.J.; Chaykovsky, M. J. Am. Chem. Soc. 87, 1353 (1965):

CH3

O

CH3H2C

CH3

CH3

O

-CH2SCH3

89%

Allylic Chlorination DMS / n-Chlorosuccinimide is useful in converting allylic alcohols to allylic chlorides. The reaction shown is an intermediate step in the synthesis of L-426925, an antidepressant in preclinical testing (US 6239135, Eli Lilly and Company). This reaction is mechanistically similar to the Corey-Kim oxi-dation of alcohols, which uses NCS and DMS to produce aldehydes and ketones under mild condi-tions (Corey, E.; Kim, C.U. J. Am. Chem.Soc. 94, 7586 (1972).

CH3

OH

CH3

Cl

NCS, DMS

17

H3C

Br

O

H3C

O

N

O

OO

N

O

O

O

+

Mg, CuBr

DMS

Conjugate Addition Stereospecific addition of Grignard Reagents in Michael fashion has been reported in the synthesis of Tolterodine tartrate, an incontinence drug launched in 1997:

The dramatic effect of DMS in these types of reactions was recently described by Jess Dambacher and Mikael Bergdahl of San Diego University [J. Org Chem. 70 (2), 580-589 (2005)]. They demon-strated that Gilman-type silylcuprates add in high yield to a,β-unsaturated carbonyl compounds in high chemical yield and diastereomeric ratio of the products:

N

O

O

O

RH

N

O

O

O

RH

SiCH3Ph

CH3

Li[PhMe2SiCuI]

DMS, 7 hr-78 to -20C

93% yield, 94:6 dr

Thioalkylation This is an additional application for dimethyl sulfide.

OHOH

SCH3

DMS, DCC

Burdon and Moffatt, J. Am. Soc. 88, 5855 (1966), 89, 4725 (1967); Marino, Pfitzner and Olofson, Tetrahedron, 27, 4181 (1971)

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Glycosylation An important step in this carbohydrate synthesis can be done using dimethyl sulfide as a stoichiometric reagent. [Hien. M. Nguyen, Yanning Chen, Sergio G. Duron, and David Y. Gin J. Am. Chem. Soc. 123, 8766-8772 (2001)].

NHO

O

O

OOH

AcO O OH

OH

O

O

OAc

Tes

NHO

O

O

OOH

AcO O

OH

O

O

OAc

Tes

SCH3

DMS, Bz2O2

MTM Ether Protection of Alcohols Dimethyl sulfide may used to protect alcohols, in the presence of benzoyl peroxide. This protection scheme is reported in taxane 302655, an oncologic drug in preclinical trials.

19

BIBLIOGRA PHY 1. L. K. Beach and A. E. Barnett; U. S. Patent 2,667, 515, Jan. 26, 1954, C. A. 49, 367d (1955). 2. C. F. Bennett, D. W. Goheen, and W. S. MacGregor; J. Org. Chern. 28, 2485 (1963). 3. C. F. Bennett and D. W. Goheen; U. S. Patent 3, 226, 433, Dec. 28, 1965. 4. W. S. MacGregor; U. S. Patent 3, 069, 473, Dec. 18, 1962. 5. V. F. Boberg, Ann. 679, 107-8 (1964). 6. W. E. Truce, G. A. Birurn, and E. T. McBee; J. Am. Chem. Soc. 74, 3594-9 (1952). 7. V. F. Boberg, G. Winter, and J. Moos; Ann. 616, 1-17 (1958). 8. C. T. Mason, Air Force Office of Scientific Research Report No. 419526 (1962). 9. V. F. Boberg, G. Winter, and G. R. Schultze; Ann. 621, 8-19 (1959). 10. S. W. Long and R. D. Moss; U. S. Patent 2, 976, 325, Mar. 21, 1961. 11. H. Bohme and H. G. Greve; Ber. 85, 409-15 (1952). 12. H. Bohnie and E. Mundlos; Ber. 86, 1414-19 (1953). - - 13. H. Gross and G. Matthey; Ber. 97, No. 9, 2606-13 (1964). 14. T. Hasseistrom, R. C. . Clapp, L. T. Mann, Jr., and L. Long, Jr.; J. Org. Chem. 26, 3026 (1961). 15. M. R. Altamura, T. Hasseistrom, and L. Long, Jr.; J. Org. Chem. 28(9), 2438-40 (1963). 16. H. Tilles and J. Antognini; U. S. Patent 2, 989, 393 June 20, 1961. 17. 22. A. Frank, B. Homeyer, and R. Heusch; Beig. Patent 633, 613, Dec. 16, 1963, CA. 61, 3637d (1964). 18. K. Szabo; U. S. Patent 3,106, 585, Oct. 8, 1963. 19. D. S. Tarbell and C. Weaver; J. Am. Chem. Soc. 63, 2939-42 (1941). 20. T. B. Douglas; J. Am. Chem. Soc. 68, 1072-6 (1946). 21. T. H. Smedsiund; U. S. Patent 2, 581, 050, Jan. 1, 1952, C. A. 46, 8669c (1952). 22. W. J. Linn; U. S. Patent 3, 115, 517, Dec. 24, 1963. 23. P. J. Graham, W. J. Linn, and W. J. Middleton; U. S. Patent 3, 282, 961, Nov. 1, 1966. 24. H. Bohme and W. Krause; Ber. 82, 426-32 (1949). 25. E. J. Corey and M. Chaykovsky; J. Am. Chem. Soc. 87, 13 53-64 (1965). 26. N. F. Blau and C. G. Stuckwisch; J. Am. Chem. Soc. 73, 2355-6 (1951). 27. D. T. McAllan, T. V. Cullum, R. A. Dean, and F. A. Fidler; J. Am. Chem. Soc. 73, 3627-32 (1951). 28. L. Tschugaeff and W. Subbotin; Ber. 43, 1200 (1910). 29. F. Kiages, A. Gleissner, and R. Ruhnau; Ber. 92, 1834-41 (1959). 30. E. L. Muetterties; U. S. Patent 3, 154, 561, Oct. 27, 1964. 31. W. H. Knoth, Jr. ; British Patent 956, 393, April 29, 1964. 32. W. H. Knoth, Jr. ; British Patent 956, 391, April 29, 1964. 33. W. H. Knoth, Jr. and E. L. Muetterties; J. Inorg. Nucl. Chem. 20, 66-72, 1961. 34. M. V. Likhosherstov; Zhur. Obschchei Khim. (J. Gen. Chem.) 17, 1478-89 (1947), C. A. 43, 172d (1949). 35. L. Homer and A. Christman; Angew. Chem. Z (10), 599-608 (1963). 36. R. Appel and W. Buchner; Ber. 95, 849-54 (1962). 37. J. A. Cogliano and G. L. Braude; U. S. Patent 3, 379, 759, April 23, 1968. 38. H. Kawabe and M. Yanagita; J. Scientific Research Inst. (Tokyo) Vol. 51, 182-8, Sept. 1957. 39. H. Kawabe and M. Yanagita; Sci. Papers Inst. Phys. Chem. Research (Tokyo) 53, 240-4 (1959). 40. M. J. Hatch and E. L. McMaster; U. S. Patent 3, 078, 259, Feb. 19, 1963. 41. R. W. Morgan and M. J. Hatch; U. S. Patent 3,146,157, Aug. 25, 1964. 42. I. D. Webb; U. S. Patent3, 075, 019, Jan. 22, 1963. 43. von V. Franzen, H. Joschek, and C. Mertz; Ann. 654, 82-91 (1962).

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