Structural effects on rates and equilibriums. 24. Double bond-stabilizing abilities of formyl, carbo-tert-butoxy, and carbomethoxy substituents

J Hine, VM Kanagasabapathy, P Ng

Index: Hine, Jack; Kanagasabapathy, V.M.; Ng, Peter Journal of Organic Chemistry, 1982 , vol. 47, # 14 p. 2745 - 2748

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Citation Number: 15

Abstract

Equilibrium constants for reactions of the type trans-MeCH= CHCH2COX+ trans-EtCH= CHCOX, where X is H, OMe, and 0-t-Bu, have been determined in tert-butyl alcohol solution at various temperatures by using basic catalysts. These equilibrium constants for formation of the conjugated isomer, extrapolated to 25" C, are 24, 4.9, and 5.1 for the aldehyde, methyl ester, and tert-butyl ester, respectively. Possible explanations for the relative magnitudes ...