Metalation of o-halostyrene oxides. Preparation of benzocyclobutenols

E Akguen, MB Glinski, KL Dhawan…

Index: Akguen, Eyup; Glinski, Margaret B.; Dhawan, Kasturi L.; Durst, Tony Journal of Organic Chemistry, 1981 , vol. 46, # 13 p. 2730 - 2734

Full Text: HTML

Citation Number: 43

Abstract

o-Bromo-and o-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBrz in THF or ether at-78" C, followed by warming to room temperature. The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization. Benzocyclobutenol ...