Tetrahedron

The effect of ortho substituents in SRNl reactions. Some synthetic applications

JF Bunnett, E Mitchel, C Galli

Index: Bunnett, Joseph F.; Mitchel, Eric; Galli, Carlo Tetrahedron, 1985 , vol. 41, # 19 p. 4119 - 4132

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Citation Number: 33

Abstract

Several ortho-substituted iodobenzenes were allowed to react, via the SRNl mechanism, with mixtures of diethyl phosphite ion and pinacolone enolate ion. From product composition data, the relative reactivities of the two nucleophiles were reckoned. They represent relative reactivities in attachment to aryl radical intermediates. Most of the ortho effects are slight, but there is evidence that large ortho substituents hinder attachment of the phosphite more ...