文献类型：期刊文献

英文题名：Dihalogenation of gem-aryl-disubstituted methylenecyclopropanes by DEAD, DIAD/TiX4 or free halogen

作者：Shao, LX; Zhao, LJ; Shi, M

机构：[1]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China;[2]E China Univ Sci & Technol, Sch Chem & Pharmaceut, Shanghai 200237, Peoples R China

年份：2004

卷号：2004

期号：23

起止页码：4894

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000225535400020)，CCR-EXPANDED(收录号:WOS:000225535400020)】；

语种：英文

外文关键词：dihalogenation; ring-opening reactions; Lewis acids; diisopropyl azodicarboxylate (DIAD); diethyl azodicarboxylate (DEAD)

摘要：The reaction of gem-aryl-disubstituted methylenecyclo-propanes with TiX4/diethyl azodicarboxylate and TiX4/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 the same products in good yields. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim., Germany, 2004)