Reactions of Phenylhydrazones with Electron-Deficient Alkenes

Barry B. Snider, Robin S.E. Conn, Stuart Sealfon

Research output: Contribution to journalArticlepeer-review

62 Scopus citations

Abstract

Reaction of aliphatic aldehyde phenylhydrazones with methyl acrylate or acrylonitrile gives phenylazoalkanes (1) by an ene reaction. With more electron-deficient alkenes such as methyl vinyl ketone or β-nitrostyrene, Michael reaction at nitrogen occurs followed by cyclization to give pyrazolidines. The reactions of phenylhydrazone monoanions with acrylonitrile take a variety of pathways depending on the counterion. The cuprous salt reacts from carbon to give 1, the lithium salt initiates polymerization, and the diethylaluminum salt alkylates on nitrogen.

Original languageEnglish
Pages (from-to)218-221
Number of pages4
JournalJournal of Organic Chemistry
Volume44
Issue number2
DOIs
StatePublished - 1979
Externally publishedYes

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