Solvent and crown ether/cryptand effects on the oximate-promoted 1, 2-elimination from β-phenylmercaptoethyl p-nitrophenolate. Formation and reactivity of a crown …

E Buncel, A Kumar, HQ Xie, RY Moir…

Index: Buncel, Erwin; Kumar, Anurag; Xie, Hai-Qi; Moir, Robert Y.; Purdon, J. Garfield Canadian Journal of Chemistry, 1994 , vol. 72, # 2 p. 437 - 447

Full Text: HTML

Citation Number: 3

Abstract

The reactions of β-phenylmercaptoethyl p-nitrophenolate (1) with three potassium oximates, viz. potassium 2, 3-butanedione monoximate (BDOK), acetophenone oximate (APOK), and acetone oximate (AOK) have been investigated in two nonhydroxylic dipolar aprotic solvents, tetraglyme and dimethyl sulfoxide (DMSO). The reaction products, as determined by 1H NMR spectroscopy, were p-nitrophenoxide ion and phenyl vinyl sulfide, in accord ...