Rearrangement of 1-aryl-2, 2-dihalo-1-alkanones

N De Kimpe, R Verhe, L De Buyck…

Index: Kimpe, Norbert De; Verhe, Roland; Buyck, Laurent De; Schamp, Niceas Journal of Organic Chemistry, 1980 , vol. 45, # 14 p. 2803 - 2813

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Citation Number: 15

Abstract

Reaction of l-aryl-2, 2-dichloro-l-alkanones with alkoxides in the corresponding alcohol afforded a mixture of l-aryl-2, 2-dialkoxy-l-alkanones and l-aryl-l, l-dialkoxy-2-alkanones. The mechanism was shown to proceed via a-chloro-a'-alkoxy epoxides, which rearranged into l- alkoxy-l-aryl-l-chloro-2-alkanones, the latter giving the final compounds via either another epoxide intermediate or a solvolysis mechanism. a, a-Dibromo-and a-bromo-a-chloroalkyl ...