Journal of the American Chemical Society

Catalysis of the debromination of 4-alkyl-4-bromo-2, 5-cyclohexadienones in aqueous solution by. alpha.-cyclodextrin

OS Tee, JM Bennett

Index: Tee, Oswald S.; Bennett, Janice M. Journal of the American Chemical Society, 1988 , vol. 110, # 10 p. 3226 - 3230

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Citation Number: 11

Abstract

Abstract: a-Cyclodextrin (CD) has little or no effect on the rates of enolization of transient 4- bromo-2, 5-cyclohexadienones (2), formed during the aqueous bromination of alkylphenols. In contrast, saturation kinetics and large catalytic effects are observed for the debromination of the title dienones (4), formed by ipso bromine attack on 4-alkylphenols (alkyl= Me, Et, i-Pr, n-Pr, t-Bu, 3, MiMe). With the exception of the n-propyl case, the extent of the catalysis (k,/k ...