The Journal of Organic Chemistry

Preparation and rearrangement of 1, 2-dialkenylcyclobutanols. A useful method for synthesis of substituted cyclooctenones

RC Gadwood, RM Lett

Index: Gadwood, Robert C.; Lett, Renee M. Journal of Organic Chemistry, 1982 , vol. 47, # 12 p. 2268 - 2275

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Citation Number: 61

Abstract

The syntheses and anionic oxy-Cope rearrangements of 1, 2-dialkenylcyclobutanols are reported. Reaction of 2-methyl-2-(2-methylpropen-l-yl)-l-cyclobutanone (1) with vinyl-, isopropenyl-, or isobutenyllithium led to formation of cyclobutanols 2a-c. Treatment with potassium hydride induced rearrangement to 2 and E cy-clooctenones 3a-c and 4a, c. Reaction of 5-methylenespiro [3.5] nonan-l-one (8) with the same alkenyllithium reagents ...