A general synthesis of N-vinyl nitrones

Scott E. Denmark, Justin I. Montgomery

Research output: Contribution to journalArticle

Abstract

A general synthesis of a new type of heterodiene, the N-vinyl nitrone, is described. The synthetic sequence begins with the conjugate addition of benzeneselenol to nitroalkenes (in turn derived from Henry reaction of an aldehyde and a nitroalkane) to provide 2-selenenylnitroalkenes. These selenonitroalkanes are reduced to the corresponding hydroxylamines which are combined with aldehydes to form nitrones. The phenylselenenyl-containing nitrones are then oxidized to selenoxides which undergo syn-selenoxide elimination to provide N-vinyl nitrones. Three X-ray crystal structures of substituted N-vinyl nitrones were obtained. In addition, the first [4+2] cycloaddition of an N-vinyl nitrone is reported.

Original languageEnglish (US)
Pages (from-to)6211-6220
Number of pages10
JournalJournal of Organic Chemistry
Volume71
Issue number16
DOIs
StatePublished - Aug 1 2006

ASJC Scopus subject areas

  • Organic Chemistry

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