Proximity Effects. XIX. Solvolysis of 4-Cyclocten-1-yl Brosylate with Trifluoroacetic Acid1,2

来自 ACS

阅读量:

36

作者:

AC CopeJM GrisarPE Peterson

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摘要:

Solvolysis of 4-cyclocten-1-yl brosylate (I) with trifluoroacetic acid followed by hydrolysis gave the known alcohols exo- and endo-bicyclo[3.3.0]octan-2-ol (II and III) and the hitherto unknown alcohols exo-bicyclo[3.2.1]octan-8-ol (IV) and cis-bicyclo[3.3.0]octan-1-ol (V). Evidence for the structure and configuration of the unknown alcohols is presented and includes the synthesis of endo-bicyclo[3.2.1]octan-8-ol (X) from bicyclo[3.2.1]octan-8-one (VII) and cis-bicyclo[3.3.0]octan-1-ol (V) from bicyclo[3.3.0]oct-1(5)-ene oxide (XX). Solvolysis of exo-cis-bicyclo [3.3.0] oct-2-yl brosylate (XIV) also gave exo-bicyclo[3.2.1]octan-8-ol (IV) providing a basis for assignment of configuration to that alcohol. trans-2-Vinylcyclohexanol (XXIII) is obtained from solvolysis of 3-cyclocten-1-yl brosylate but not from solvolysis of the 4-isomer I. 3-Cyclocten-1-ol is therefore postulated to be a precursor of trans-2-vinylcyclohexanol (XXIII) in the solvolysis of cis-cyclooctene oxide and in the reaction of 1,5-cycloctadiene (VI) with strong acids.

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DOI:

10.1021/ja01501a046

被引量:

364

年份:

1960

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2010
被引量:21

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