Journal of Organic Chemistry p. 3519 - 3521 (1981)
Update date:2022-08-11
Topics:
Freedlander, Richard S.
Bryson, Thomas A.
Dunlap, R. Bruce
Schulman, E. M.
Lewis, Charles A.
The addition of simple alcohols in hexachloroacetone (HCA) in the presence of strong hydrogen bond acceptors (e.g., dimethylformamide) results in a high yield of the corresponding trichloroacetate (via a haloform reaction scheme).The trichloroacetylation reactions are carried out under neutral conditions, and the resultant ester can easily be separated from the reaction mixture via extraction/distillation procedures.Kinetic evidence demonstrates that the trichloroacetylation of alcohols by HCA is a stereoselective process, and further studies suggest that the catalytic role of the acceptors is of a hydrogen bonding nature.
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