Tetrahedron letters

Thermal reactions of benzocyclobutenone with alcohols

ZY Wang, S Laurence, JP Gao

Index: Wang, Zhi Yuan; Suzzarini, Laurence; Gao, Jian Ping Tetrahedron Letters, 1997 , vol. 38, # 33 p. 5745 - 5746

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Citation Number: 4

Abstract

Thermolysis or photolysis of benzocyclobutenone (1) generates a reactive intermediate of considerable interest in organic synthesis, ¢t-oxo-o-quinodimethane (2), which undergoes facile [4+2] cycloaddition reaction with aldehydes, ketones and dienophiles such as maleic anhydride, dimethyl fumarate, benzoquinones and [60]fullerene.l,2, 3 Besides the diene moiety, another intriguing group in 2 is the ketene. Ketches are highly reactive towards a variety of compounds such ...