Efficient synthesis of 2-vinylcyclobutanones by the rearrangement of 1-methoxy-1-cyclopropylcarbinols under neutral conditions

T Cohen, L Brockunier

Index: Cohen, Theodore; Brockunier, Linda Tetrahedron, 1989 , vol. 45, # 10 p. 2917 - 2924

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Citation Number: 12

Abstract

A common synthesis of cyclobutanones involves the rearrangement of 1-alkoxy-or 1- (phenylthio) cyclopropylcarbinols under acidic conditions. We report that the synthetically useful 2-vinylcyclobutanones can be prepared in good yield in the absence of protonic acids by treating vinyl-1-(methoxycyclopropyl) carbinols with triflic anhydride in the presence of 2, 6-di-tert-butyl-4-methylpyridine in methylene chloride. The product is formed before ...