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H-Bonding Activation in Highly Regioselective Acetylation of Diols.
- Source :
-
Journal of Organic Chemistry . 11/15/2013, Vol. 78 Issue 22, p11618-11622. 5p. - Publication Year :
- 2013
-
Abstract
- 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 amount 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 78
- Issue :
- 22
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 93460736
- Full Text :
- https://doi.org/10.1021/jo402036u