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Dihalogenation of gem ‐Aryl‐Disubstituted Methylenecyclopropanes by DEAD, DIAD/TiX 4 or Free Halogen
Author(s) -
Shao LiXiong,
Zhao LinJing,
Shi Min
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400388
Subject(s) - chemistry , diad , bromine , halogen , diethyl azodicarboxylate , aryl , iodine , organic chemistry , ring (chemistry) , medicinal chemistry , catalysis , alkyl , triphenylphosphine , copolymer , polymer
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 the same products in good yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)