Electrochemical Generation and Reaction of <i>o</i>-Quinodimethanes from {[[2-(2,2-Dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes
作者:Madoka Jinno、Yoshikazu Kitano、Masahiro Tada、Kazuhiro Chiba
DOI:10.1021/ol990647s
日期:1999.8.1
The anodic oxidation of [[2-(2,2-dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes gave o-quinodimethanes which were trapped in situ by dienophiles to give the corresponding cycloadducts in excellent yields. The electron transfer and succeeding 1,4-elimination reaction was efficiently completed in a solution of lithium perchlorate/nitromethane in the presence of acetic acid. The reaction progress was quantitatively controlled by the passage of charge. By using this new method, an aryltetralin lignan skeleton was also synthesized.