Nature of the slow step in the hydrolysis of cyclic and bicyclic ortho esters containing 1, 3-dioxane rings

RA McClelland, S Gedge…

Index: McClelland, Robert A.; Gedge, Sherrin; Bohonek, Jon Journal of Organic Chemistry, 1981 , vol. 46, # 5 p. 886 - 891

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Citation Number: 7

Abstract

Both types of compounds exhibit a change in the slow step in product formation with changing pH. At high pH the 1, 3-dioxan-2-ylium ion forming step is rate determining, while at low pH the slow step involves the decomposition of the hydrogen ortho ester intermediate of the hydrolysis, and both this intermediate and the 1, 3-dioxan-2-ylium ion intermediate accumulate in significant amounts during hydrolysis. A similar change in the slow step has ...