Hydrolysis of cyclic orthoesters: Experimental observations and theoretical rationalization

Article abstract of DOI:10.1016/0040-4020(96)00915-5

Reaction products using labelled water (H₂O¹⁸) and the relative rate of hydrolysis of the four bicyclic orthoesters 1-4 having a six or a seven-membered orthoester ring are reported. With the help of theoretical calculations (semi-empirical AM1 and ab initio 3-21G level), the results are explained by taking into account proton affinities as well as steric and stereoelectronic effects.