O. Tsuge, Hiroyuki Watanabe, Y. Kiryu
Dec 1, 1979
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The reactions of highly strained 1,2-diphenyl-1-azaspiro[2.2]pentane (1) and 2-phenyl-1-azaspiro[2.2]pent-1-ene (2) with C,N-diarylnitrilimines (3) were described. The reaction of 1 with 3 gave the corresponding 4,5,7,8-tetraphenyl-4,6,7-triazaspiro[2.5]oct-5-ene, 1,5,7,8-tetraphenyl-5,6,8-triazaspiro[3.4]oct-6-ene, 1,3,5-triphenyl-2-pyrazoline, 1,3,4-triphenyl-1,2,4-triazolin-5-one, and/or 1,3,4,6,8-pentaphenyl-1,2,4,6,7-pentaazaspiro[4.4]nona-2,7-diene, whose yields depended on the reaction conditions. The pathways for the formation of products are also postulated. The azaspiropentene 2 readily reacted with 3 to give the corresponding 1,2,4-triphenyl-2,3,5-triazabicyclo[4.2.0]octa-3,5-diene arising from the rearrangement of initial 1,3-cycloadduct.