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Synthesis 2005(10): 1713-1717
DOI: 10.1055/s-2004-834869
DOI: 10.1055/s-2004-834869
PSP
© Georg Thieme Verlag Stuttgart · New YorkA Convenient Way for the Conversion of Carboxylic Esters into 2-Substituted Allyl Halides
Further Information
Received
1 June 2004
Publication Date:
03 November 2004 (online)
Publication History
Publication Date:
03 November 2004 (online)

Abstract
The preparation of functionalized 2-substituted allyl bromides and chlorides from carboxylic esters is reported. The carboxylic esters were transformed first to 1-substituted cyclopropanols by treating with ethylmagnesium bromide in the presence of titanium alkoxide. Mesylation of the cyclopropanols followed by halide displacement of the sulfonate group to halogen, accompanied by cyclopropyl-allyl rearrangement, affords the required allyl bromides and chlorides.
Key words
cyclopropanation - titanium alkoxides - cyclopropanols - cyclopropyl-allyl rearrangement - allyl halides
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