Torquoselectivity in the electrocyclic conversion of benzocyclobutenes to o-xylylenes

…, G Bernardinelli, Y Wang, DC Spellmeyer…

Index: Jefford, Charles W.; Bernardinelli, Gerald; Wang, Ying; Spellmeyer, David C.; Buda, Andrzej; Houk Journal of the American Chemical Society, 1992 , vol. 114, # 4 p. 1157 - 1165

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Citation Number: 111

Abstract

Abstract: 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 ...

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