An unexpected two-group migration involving a sulfonynamide to nitrile rearrangement. Mechanistic studies of a thermal N → C tosyl rearrangement

Michael Bendikov, Hieu M. Duong, Eduardo Bolanos, Fred Wudl

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

(Chemical Equation Presented) We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrite and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100°C in the melt).

Original languageEnglish
Pages (from-to)783-786
Number of pages4
JournalOrganic Letters
Volume7
Issue number5
DOIs
Publication statusPublished - Mar 3 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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