Cyclopropanones. Formation of vinylcyclopropanols and their rearrangement to cyclobutanones

HH Wasserman, MJ Hearn…

Index: Wasserman, Harry H.; Hearn, Michael J.; Cochoy, Robert E. Journal of Organic Chemistry, 1980 , vol. 45, # 14 p. 2874 - 2880

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Citation Number: 39

Abstract

Vinylcyclopropanols, formed by the addition of vinylmagnesium bromide to the ethyl hemiketal of cyclopropanone, may be converted to cyclobutanone derivatives on reaction with various electrophiles. The ring enlargement of 1-vinyl-2-methylcyclopropanol takes place by preferential migration of the more highly substituted carbon atom.

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