Vinylcyclobutanols: A composite functional group?

BM Trost, DWC Chen

Index: Trost, Barry M.; Chen, Deborah W. C. Journal of the American Chemical Society, 1996 , vol. 118, # 50 p. 12541 - 12554

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Citation Number: 42

Abstract

The effect of small strained rings on chemical reactivity was probed by the examination of the behavior of vinylcyclobutanols as terminators in cyclization reactions. The substrates were readily available by the addition of vinyllithium reagents bearing acetals as cyclization initiators to cyclobutanone. Bronsted and Lewis acids both promoted cyclization in contrast to vinylcyclopropanol terminators for which Bronsted acids failed. The products are ...