Reactions of (E)-1,2-di(3-guaiazulenyl)ethylene and 2-(3-guaiazulenyl)-1,1-bis(4-methoxyphenyl)ethylene with tetracyanoethylene (TCNE) in benzene: comparative studies on the products and their spectroscopic properties

摘要

Reactions of the title ethylene derivatives, (E)-1,2-di(3-guaiazulenyl)ethylene (1) and 2-(3-guaiazulcnyl)-1,1-bis(4-methoxyphenyl)ethylene (2), with a 2 M amount of TCNE in benzene at 25 degrees C for 24 h under argon give new cycloaddition compounds, 1, 1,2,2,11,11,12,12-octacyano-3-(3-guaiazulenyl)-8-isopropyl-5, 10-dimethyl- 1,2,3,6,9, 10a-hexahydro-6,9-ethanobenz[a]azulene (3) from 1 and 1,1,2,2,11,11,12,12-octacyano-8-isopropyl-3,3-bis(4-methoxyphenyl)-5,10-dimethyl-1,2,3,6,9,10a-hexahydro-6,9-ethanobenz[a]azulene (4) from 2, respectively, in 66 and 87% isolated yields. Comparative studies on the above reactions as well as the spectroscopic properties of the unique products 3 and 4, possessing interesting molecular structures, are reported and, further, a plausible reaction pathway for the formation of these products is described. (c) 2006 Elsevier Ltd. All rights reserved.