Selective Skeletal Rearrangement of Tricyclo[5.4.0.0<sup>1,5</sup>]undecanes to Tricyclo[5.3.1.0<sup>1,5</sup>]- and [5.4.0.0<sup>3,8</sup>]undecanes
作者:Kiyomi Kakiuchi、Shuichi Kumanoya、Kazuya Kobiro、Yoshito Tobe、Yoshinobu Odaira
DOI:10.1246/bcsj.63.3358
日期:1990.11
rearrangement of tricyclo[5.4.0.01,5]undecan-ll-one gave tricyclo[5.3.1.01,5]undecan-11-one in a nonnucleophilic media and tricyclo[5.4.0.03,8]undecane-7, 8-diol in the presence of a nucleophile, respectively. Tricyclo[5.4.0.01,5]undecan-11-ols also rearranged to tricyclo[5.4.0.03,8]undecan-7-ol. A reductive rearrangement with a hydride transfer of the alcohol gave only tricyclo[5.4.0.03,8]undecane.
三环[5.4.0.01,5]十一烷-11-one的酸催化重排在非亲核介质中得到三环[5.3.1.01,5]十一烷-11-1和三环[5.4.0.03,8]十一烷-7, 8-二醇分别在亲核试剂存在下。三环[5.4.0.01,5]十一烷-11-醇也重排为三环[5.4.0.03,8]十一烷-7-醇。醇的氢化物转移的还原重排仅产生三环[5.4.0.03,8]十一烷。