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

Amal I. Siriwardana, Itaru Nakamura, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

The reaction of alkylidenecyclopropanes with HCl or with HBr proceeds very smoothly at 120°C 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.

Original languageEnglish
Pages (from-to)985-987
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number5
DOIs
Publication statusPublished - 2003 Jan 27

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Addition of hydrogen halides to alkylidenecyclopropanes: A highly efficient and stereoselective method for the preparation of homoallylic halides'. Together they form a unique fingerprint.

Cite this