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

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Aldehydes
Hydroxylamines
Cycloaddition
nitrones
Crystal structure
X rays
benzeneselenol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A general synthesis of N-vinyl nitrones. / Denmark, Scott E; Montgomery, Justin I.

In: Journal of Organic Chemistry, Vol. 71, No. 16, 01.08.2006, p. 6211-6220.

Research output: Contribution to journalArticle

Denmark, Scott E ; Montgomery, Justin I. / A general synthesis of N-vinyl nitrones. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 16. pp. 6211-6220.
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