1
1999 rearrangements rearrangements O 0140 25 - 049 Degradative Rearrangements of N-(t-Butyloxycarbonyl)-O- methanesulfonylhydroxamic Acids: A Novel, Reagent-Based Al- ternative to the Lossen Rearrangement. N-acyl hydroxamates (I) are found to be valuable stable precursors for a novel thermally induced rearrangement in the presence of alcohols [cf. conditions A)]. Protected amines are obtained in good to excellent yield without addition of any Lewis acid. (STAFFORD, JEFFREY A.; GONZALES, STEPHEN S.; BARRETT, DAVID G.; SUH, EDWARD M.; FELDMAN, PAUL L.; J. Org. Chem. 63 (1998) 26, 10040-10044; Glaxo Wellcome Inc., Research Triangle Park, NC 27709, USA; EN) 1

ChemInform Abstract: Degradative Rearrangements of N-(t-Butyloxycarbonyl)-O-methanesulfonylhydroxamic Acids: A Novel, Reagent-Based Alternative to the Lossen Rearrangement

Embed Size (px)

Citation preview

Page 1: ChemInform Abstract: Degradative Rearrangements of N-(t-Butyloxycarbonyl)-O-methanesulfonylhydroxamic Acids: A Novel, Reagent-Based Alternative to the Lossen Rearrangement

1999 rearrangements

rearrangementsO 0140

25 - 049Degradative Rearrangements of N-(t-Butyloxycarbonyl)-O-methanesulfonylhydroxamic Acids: A Novel, Reagent-Based Al-ternative to the Lossen Rearrangement. — N-acyl hydroxamates(I) are found to be valuable stable precursors for a novel thermally inducedrearrangement in the presence of alcohols [cf. conditions A)]. Protected aminesare obtained in good to excellent yield without addition of any Lewis acid. —(STAFFORD, JEFFREY A.; GONZALES, STEPHEN S.; BARRETT, DAVIDG.; SUH, EDWARD M.; FELDMAN, PAUL L.; J. Org. Chem. 63 (1998) 26,10040-10044; Glaxo Wellcome Inc., Research Triangle Park, NC 27709, USA;EN)

1