Dihalogenation of gem??Aryl??Disubstituted Methylenecyclopropanes by DEAD, DIAD/TiX4 or Free Halogen

LX Shao, LJ Zhao, M Shi

Index: Shao, Li-Xiong; Zhao, Lin-Jing; Shi, Min European Journal of Organic Chemistry, 2004 , # 23 p. 4894 - 4900

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Citation Number: 10

Abstract

Abstract The reaction of gem-aryl-disubstituted methylenecyclopropanes with TiX 4/diethyl azodicarboxylate and TiX 4/diisopropyl azodicarboxylate in 1, 2-dichloroethane gave the dihalogenated ring-opened product, 2, 4-dihalobut-1-ene, in moderate-to-excellent yields under mild conditions. On the basis of the proposed Orton-type mechanism, we found that this reaction can also be carried out with free halogens such as bromine or iodine to give ...