Chlorotrimethylsilane:  A Suitable Reagent for the Synthesis of Chlorohydrin Esters

Chlorotrimethylsilane:  A Suitable Reagent for the Synthesis of Chlorohydrin Esters

A new methodology for obtaining chlorohydrin esters using a one-pot esterification−chlorination reaction, in which one of the reagents, chlorotrimethylsilane, acts as solvent, is described. The reaction is stereospecific and its regioselectivity depends on the number of carbons between the hydroxyl...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 67; no. 24; pp. 8631 - 8634
Main Authors: Eras, Jordi, Méndez, Jonh Jairo, Balcells, Mercè, Canela, Ramon
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 29-11-2002
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
One pot reaction
Ester
Diol
Chlorination
Regioselectivity
Chlorine Organic compounds
Reaction mechanism
Alcohol
Organic silane
Stereospecificity
Chemical synthesis
Esterification
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Summary:A new methodology for obtaining chlorohydrin esters using a one-pot esterification−chlorination reaction, in which one of the reagents, chlorotrimethylsilane, acts as solvent, is described. The reaction is stereospecific and its regioselectivity depends on the number of carbons between the hydroxyl groups present in the starting material. A mechanism is proposed.
Bibliography:istex:54D6EDFB5597718D24E2EB78A6B5AD1B1E147C6B
ark:/67375/TPS-Q7415P1R-K
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo026020w