The Journal of Organic Chemistry

Synthesis of substituted cyclooctenones: substituent effects in the [3, 3]-sigmatropic rearrangement of divinylcyclobutanols

SA Miller, RC Gadwood

文献索引：Miller, Scott A.; Gadwood, Robert C. Journal of Organic Chemistry, 1988 , vol. 53, # 10 p. 2214 - 2220

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被引用次数: 12

摘要

From cyclobutanone 1 12 divinylcyclobutanols were prepared. Substituent effects on the rate of oxy-Cope rearrangement to form cyclooctenones were monitored by NMR. Divinylcyclobutanols 2a, 4a, 5a, 6a, and 8a gave first-order rate constants with the rates of rearrangements being in the order 4a< 5a< 2a< 6a< 3a< 8a. Cyclobutanols 7a, 9a, loa, and 12a all rearranged too fast to isolate. The steric effects on the rate of rearrangement and ...