Thermally induced [2+2] cycloadditions of (benzyloxymethylene)cyclopropane with alkylidenemalononitriles

Itaru Nakamura, Ryoko Nagata, Tetsuya Nemoto, Masahiro Terada, Yoshinori Yamamoto, Thomas Späth, Armin De Meijere

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The reaction of (benzyloxymethylene)cyclopropane (1a) with alkylidenemalononitriles 2 at ambient pressure afforded the corresponding cyclobutane derivatives 3 in good-to-high yields. For example, the reaction of 1a with benzylidenemalononitrile (2a), (2-naphthylmethylene)malononitrile (2e), and tert-butylmethylenemalononitrile (2f) in acetonitrile at 80°C gave the corresponding cyclobutanes 3a, 3e, and 3f in 96, 96, and 91% yield, respectively. Control experiments proved that the reaction proceeds via well-stabilized zwitter-ionic intermediate 6.

Original languageEnglish
Pages (from-to)4479-4482
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number27
DOIs
Publication statusPublished - 2007 Oct 2

Keywords

  • Cycloaddition
  • Cyclobutanes
  • Cyclopropanes
  • Enols

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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