Journal of the American Chemical Society p. 1157 - 1165 (1992)
Update date:2022-08-05
Topics:
Jefford, Charles W.
Bernardinelli, Gerald
Wang, Ying
Spellmeyer, David C.
Buda, Andrzej
Houk
The conrotatory electrocyclic opening of benzocyclobutene to o-xylylene was studied by means of ab initio molecular orbital calculations. The theory developed earlier to predict the torquoselectivity of ring opening of 3-substituted cyclobutenes was found to be applicable. Experimentally, the ring opening of several 7-substituted benzocyclobutenes, such as the cyano, methoxycarbonyl, and formyl derivatives was examined. o-Xylylenes were obtained in which cyano or ester groups had rotated outwards, whereas the formyl group turned inwards. N,N-Dimethylbenzocyclobutene-7-carboxamide exhibited 75% inward torquoselectivity upon ring opening. A reversal of mode was seen with the 7-methyl derivatives of benzocyclobutene-7-carbonitrile and methyl benzocyclobutene-7-carboxylate in that the 7-methyl substituent manifested overwhelming outward motion.
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