Proximity Effects. XVII. Products and Rates of Solvolysis of Cycloctenyl Derivatives1,2

来自 ACS

阅读量:

31

作者:

AC CopePE Peterson

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摘要:

The study of proximity effects in cycloctane derivatives has been extended to compounds containing double bonds in the eight-membered ring. The products of solvolysis of 4-cyclocten-1-yl brosylate, 3-cyclocten-1-yl brosylate, 3-bromocyclooctene and cycloctyl brosylate in acetic acid containing sodium acetate were studied. First-order rate constants for the solvolysis of these compounds and for the solvolysis of cycloctyl bromide were determined. 4-Cyclocten-1-yl brosylate yielded bridged compounds having the bicyclo[3.3.0]octane ring system as the major solvolysis products, while 3-cyclocten-1-yl brosylate formed bicyclo[5.1.0]octan-2-ol as a principal product. Although 4-cyclocten-1-yl brosylate gave bridged products that might arise from double bond participation, its solvolysis rate was only about one-sixtieth that of cycloctyl brosylate. Syntheses of 3-cyclocten-1-ol and 4-cyclocten-1-ol were developed. The products of reaction of formic acid with 1,5-cycloctadiene were studied, and trans-2-vinylcyclohexanol was identified as one of them.

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DOI:

10.1021/ja01516a034

被引量:

149

年份:

1959

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