SOME REPRESENTATIVE CYCLOADDITIONS OF VINYLCYCLOPROPANE. AN EVIDENCE FOR THE TWO-STEP PROCESS IN THE DONOR-ACCEPTOR TYPE CYCLOADDITION
作者:Nobujiro Shimizu、Shin-ichi Ishizuka、Takashi Tsuji、Shinya Nishida
DOI:10.1246/cl.1975.751
日期:1975.7.5
Reaction of 1,1-diphenyl-2-vinylcyclopropane with 2,3,4,5-tetrachlorocyclopentadienone ethylene ketal proceeded smoothly to give a diene adduct quantitatively, whereas its reaction with tetracyanoethylene gave unexpected adducts after rearrangements. These results evidence that the latter donor-acceptor type cycloaddition proceeds via a zwitterionic intermediate.
1,1-二苯基-2-乙烯基环丙烷与2,3,4,5-四氯环戊二烯酮乙烯缩酮反应顺利进行,定量得到二烯加合物,而与四氰乙烯反应重排后得到意想不到的加合物。这些结果证明后一种供体-受体型环加成是通过两性离子中间体进行的。