A Convenient Way for the Conversion of Carboxylic Esters into 2-Substituted Allyl Halides

Oleg G. Kulinkovich; Yurii Y. Kozyrkov; Andrei V. Bekish; Evgenii A. Matiushenkov; Ivan L. Lysenko

doi:10.1055/s-2004-834869

PSP

A Convenient Way for the Conversion of Carboxylic Esters into 2-Substituted Allyl Halides

Oleg G. Kulinkovich*, Yurii Y. Kozyrkov, Andrei V. Bekish, Evgenii A. Matiushenkov, Ivan L. Lysenko
Department of Organic Chemistry, Belarusian State University, Skoriny av. 4, 220050 Minsk, Belarus
Fax: +375(172)265609; e-Mail: kulinkovich@bsu.by;

Abstract

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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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References

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