Methylidenecycloproparenes: Novel Compounds with Fascinating Properties

Brian Halton; Peter J. Stang

doi:10.1055/s-1997-723

Synlett 1997; 1997(2): 145-158
DOI: 10.1055/s-1997-723

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Methylidenecycloproparenes: Novel Compounds with Fascinating Properties

Brian Halton¹ , Peter J. Stang²

¹Department of Chemistry, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand
²Department of Chemistry, The University of Utah, Salt Lake City, UT 84112, USA

Abstract

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Proton abstraction from the methylene position of a cycloproparene provides the corresponding C1 anion that can be intercepted by a carbonyl-containing compound to provide a wide range of novel methylidenecycloproparenes. The physical and chemical aspects of this comparatively new class of surprisingly stable, strained compounds have been explored. The present account provides a perspective on these developments from the initial experiments in the Utah laboratories.

cycloproparenes - benzocyclopropenes - methylidene derivatives

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