The Hydrolysis of Cyclic Orthoesters. Stereoelectronic Control in the Cleavage of Hemiorthoester Tetrahedral Intermediates
Open Access
- 1 June 1975
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 53 (11) , 1601-1615
- https://doi.org/10.1139/v75-226
Abstract
The synthesis of several cyclic dialkoxy orthoesters is reported. Acid hydrolysis of these orthoesters under kinetically controlled conditions gives the corresponding hydroxy esters only. Conformationally rigid cyclic mixed orthoesters give a hydroxy ester by exclusive loss of the axial alkoxy group. A cyclic orthoester can have nine different gauche conformations. It is shown that they are hydrolyzed through only one gauche conformer. These results bring further experimental evidence that there is a stereoelectronic control in the cleavage of tetrahedral intermediates in the hydrolysis of esters.Keywords
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