The products of hydrolysis of cyclic orthoesters as a function of pH and the theory of stereoelectronic control

P Deslongchamps, J Lessard…

Index: Deslongchamps, Pierre; Lessard, Jean; Nadeau, Yves Canadian Journal of Chemistry, 1985 , vol. 63, p. 2485 - 2492

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Citation Number: 30

Abstract

The acid hydrolysis of cyclic orthoesters 1, 3-6 (R= Me), and 2 (R= Me and Et) as a function of pH was studied. The bicyclic orthoester 5 yields mainly the hydroxy-ester (less than 5% lactone), and this result is essentially independent of pH. For the other orthoesters, the relative percentage of products differs for each case and varies with pH. At pH≤ 3, the percentage of lactone is always larger than at pH> 3. These results are explained on the ...