Kinetic and equilibrium studies of the σ-adduct forming reactions of 1, 3, 5-trinitrobenzene and picryl chloride with some carbon bases

MR Crampton, TP Kee…

Index: Crampton, Michael R.; Kee, Terence P.; Wilcock, Jennifer R. Canadian Journal of Chemistry, 1986 , vol. 64, p. 1714 - 1720

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Citation Number: 15

Abstract

Reaction of 1, 3, 5-trinitrobenzene (TNB) with the malononitrile anion in methanol yields a carbon-bonded σ-adduct,(3). Ionisation of the remaining exocyclic hydrogen is favourable and yields the dianion (4). The initial reaction of 1-chloro-2, 4, 6-trinitrobenzene similarly occurs at an unsubstituted ring position, but is followed by slower nucleophilic attack at the 1- position yielding the substituted product. A major difference in the reaction of the ethyl ...