Elimination and addition reactions. Part XIX. Elimination of phenoxide from β-substituted ethyl phenyl ethers: the nature of activation in 1, 2-elimination

J Crosby, CJM Stirling

Index: Crosby,J.; Stirling,C.J.M. Journal of the Chemical Society [Section] B: Physical Organic, 1970 , p. 671 - 679

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Citation Number: 21

Abstract

In an investigation of the nature of activation in elimination reactions, rates of elimination of phenoxide under basic conditions from a series of 17 phenyl ethers of the type X–CH2· CH2· OPh have been measured. Second-order rate constants span a range of 1011 according to the nature of X. Good correlation is obtained between log kelimination and the parameter σR– , but not with σ or σ*, indicating that resonance stabilisation of a carbanionic species is an ...