Addition of hydrogen halides to alkylidenecyclopropanes: a highly efficient and stereoselective method for the preparation of homoallylic halides

Amal Inoka Siriwardana, Itaru Nakamura, Yoshinori Yamamoto

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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.
Original languageEnglish
Pages (from-to)985 - 987
Number of pages3
JournalTetrahedron Letters
Issue number5
Publication statusPublished - 2003
Externally publishedYes

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