H-Bonding Activation in Highly Regioselective Acetylation of Diols.
Journal article, 2013

H-bonding activation in the regioselective acetylation of vicinal and 1,3-diols is presented. Herein, the acetylation of the hydroxyl group with acetic anhydride can be activated by the formation of H-bonds between the hydroxyl group and anions. The reaction exhibits high regioselectivity when a catalytic amt. of tetrabutylammonium acetate is employed. Mechanistic studies indicated that acetate anion forms dual H-bonding complexes with the diol, which facilitates the subsequent regioselective monoacetylation. [on SciFinder(R)]

regioselective acetylation


hydrogen bonding activation

Density functional theory


Yixuan Zhou

Bin Wu

Xiaoling Zhang

Bo Ren

Hai. Dong

Journal of Organic Chemistry

0022-3263 (ISSN) 1520-6904 (eISSN)

Vol. 78 22 11618-11622

Subject Categories

Theoretical Chemistry

Organic Chemistry



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