Dark reactions of halobenzenes with pinacolone enolate ion. Evidence for a thermally induced aromatic SRN1 reaction

RG Scamehorn, JF Bunnett

Index: Scamehorn,R.G.; Bunnet,J.F. Journal of Organic Chemistry, 1977 , vol. 42, # 8 p. 1449 - 1457

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Citation Number: 70

Abstract

Halobenzenes with Pinacolone Enolate Ion J. Org. Chern., Vol. 42, No. 8, 1977 1449 cis coupling constant being 6-7 Hz and the trans coupling constant 12-14 HzSz6 The configurations of the geometric isomers of 9 were assigned as follows. The first step in the synthesis of 9 involves a reaction between the dimethyl acetal of methyl isobutyl ketone and 2-bromoethanol under acid conditions, which leads to a formation of the isomeric species i ...