Thermal isomerization of benzocyclobutene

OL Chapman, UPE Tsou…

Index: Chapman, Orville L.; Tsou, Uh-Po Eric; Johnson, Jeffery W. Journal of the American Chemical Society, 1987 , vol. 109, # 2 p. 553 - 559

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Citation Number: 16

Abstract

Abstract: Thermolysis of benzocyclobutene (I3CHz, 99%) gives styrene labeled in the/3 (48%), ortho (30%), CY (14%), meta (4%), and para (4%) positions. The major labels (0 and ortho) are consistent with a mechanism involving interconversions of the isomeric tolylmethylenes and the methylcycloheptatetraenes. This mechanism also involves interconversion of o-tolylmethylene with o-xylylene and p-tolylmethylene with p-xylylene. ...