Elimination–addition mechanisms of acyl-group transfer reactions: a novel E 1 cB mechanism in the hydrolysis of 2, 4-dinitrophenyl 4-hydroxybenzoate

…, G Guanti, G Petrillo, A Hopkins, A Williams

Index: Thea, Sergio; Guanti, Giuseppe; Petrillo, Giovanni; Hopkins, Andrew; Williams, Andrew Journal of the Chemical Society, Chemical Communications, 1982 , # 11 p. 577 - 578

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Abstract

Evidence is offered for the intermediacy of an unprecedented para-oxoketen intermediate in a dissociative mechanism for the hydrolysis of the title ester. ... We are interested in the structural, electronic, and stereo- chemical factors favouring dissociative mechanisms of acyl- group transfer. Provision of suitable electron-releasing sys- tems such as a charged atom cc to the acyl function will tend to stabilise an incipient acylium ion and promote the ...