The reaction of alkylidenecyclopropanes with HCl or with HBr proceeds very smoothly at 120degreesC to produce the corresponding homoallylic halides stereoselectively in good to excellent yields. For example, the reaction of (1-phenylbenzylidene)cyclopropane, (1-butylpentylidene)cyclopropane and octylidenecyclopropane with hydrochloric acid produced the corresponding homoallylic chlorides, 4-chloro-1,1-diphenyl-1-butene, 4-butyl-1-chloro-3-octene and (E)-1-chloro-3-undecene in 99, 96, and 87 yields, respectively. The reaction of (1-butylpentylidene)cyclopropane with hydrobromic acid yielded 1-bromo-4-butyl-3-octene in 95 yield. (C) 2003 Elsevier Science Ltd. All rights reserved.
|Pages (from-to)||985 - 987|
|Number of pages||3|
|Publication status||Published - 2003|