A convenient way for the conversion of carboxylic esters into 2-substituted allyl halides

The preparation of functionalized 2-substituted allyl bromides and chlorides from carboxylic esters is reported. The carboxylic esters were transformed first to I-substituted cyclopropanols by treating with ethylmagnesium bromide in the presence of titanium alkoxide. Mesylation of the cyclopropanols...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) no. 10; pp. 1713 - 1717
Main Authors Kulinkovich, OG, Kozyrkov, YY, Bekish, AV, Matiushenkov, EA, Lysenko, IL
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.07.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cyclopropanation
CHEMISTRY
CHLORIDES
cyclopropyl-allyl rearrangement
cyclopropanols
titanium alkoxides
allyl halides
CHLORINATION
Online AccessGet more information

Cover

More Information
Summary:The preparation of functionalized 2-substituted allyl bromides and chlorides from carboxylic esters is reported. The carboxylic esters were transformed first to I-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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2004-834869