Dehydrobromination of some substituted phenyl 3-bromopropionates and phenyl 3-bromothiolopropionates. Transmission of activation effects through acyl bonds

…, FB Peters, HW Johnson Jr

Index: Gilbert, Arthur B.; Peters, Frances B.; Johnson, H. W. Journal of Organic Chemistry, 1983 , vol. 48, # 16 p. 2724 - 2728

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Abstract

Thirteen aryl 3-bromopropionates and nine aryl 3-bromothiolopropionates were prepared and subjected to dehydrohalogenation with sodium 3, 4-dinitrophenoxide in dry tetrahydrofuran at 34.25" C. The second-order rate constants for the sulfur esters were approximately 10 times those for the corresponding oxygen esters. Good Hammett plots with p's of+ 0.81 f 0.04 and 0.98* 0.04 for the oxygen and sulfur series, respectively, were ...

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