Intermolecular [4 + 2]‐Cycloadditions of Nitroalkenes with Cyclic Olefins. Transformations of Cyclic Nitronates

Scott E. Denmark, Christopher J. Cramer, Jeffrey A. Sternberg

Research output: Contribution to journalArticlepeer-review

50 Scopus citations

Abstract

Nitrocyclohexene undergoes facile SnCl4‐induced, [4 + 2]‐cycloadditions with simple cycloalkenes to produce nitronates. The nitronates can be transformed sterospecifically into a number of other functional groups (alcohol, ketone, oxime, amine) by hydrolytic, reductive, and oxidative processes. The mechanism of the [4 + 2]‐cycloaddition is believed to involve formation of a zwitterionic intermediate which can collapse via competing pathways to form the observed products. 1,3‐Dipolar cycloadditions of the nitronates are described.

Original languageEnglish (US)
Pages (from-to)1971-1989
Number of pages19
JournalHelvetica Chimica Acta
Volume69
Issue number8
DOIs
StatePublished - Dec 10 1986

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