A General Method for the Preparation of 2,2-Disubstituted 1-Nitroalkenes

Scott E. Denmark, Lawrence R. Marcin

Research output: Contribution to journalArticle

Abstract

A general and expeditious route for the preparation of functionalized 2,2-disubstituted 1-nitroalkenes has been developed. Conjugate 1,4-addition of complex zinc cuprates (RCu(CN)ZnI) to easily obtained CE)-l-nitroalkenes, followed by trapping with phenylselenenyl bromide and subsequent oxidative elimination, afforded the corresponding 2,2-disubstituted 1-nitroalkenes in good yields. 2-Alkyl-2-aryl- and 2,2-dialkyl nitroalkenes 4b-g were prepared in 76–88% yield and obtained as E/Z isomeric mixtures, slightly favoring the Z isomer (∼1.0:1.5, E/Z).

Original languageEnglish (US)
Pages (from-to)3850-3856
Number of pages7
JournalJournal of Organic Chemistry
Volume58
Issue number15
DOIs
StatePublished - Jan 1 1993

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Bromides
Isomers
Zinc

ASJC Scopus subject areas

  • Organic Chemistry

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A General Method for the Preparation of 2,2-Disubstituted 1-Nitroalkenes. / Denmark, Scott E.; Marcin, Lawrence R.

In: Journal of Organic Chemistry, Vol. 58, No. 15, 01.01.1993, p. 3850-3856.

Research output: Contribution to journalArticle

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