The Journal of Organic Chemistry

o-Quinone Methides from 4-Allenylcyclobutenones: Synthesis and Chemistry

M Taing, HW Moore

Index: Taing, Meng; Moore, Harold W. Journal of Organic Chemistry, 1996 , vol. 61, # 1 p. 329 - 340

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Citation Number: 48

Abstract

Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of ...