The reaction of bromanil (2,3,5,6-tetrabromobenzoquinone)with 1,1,3,3-tetramethylguanidine in benzene has been studied spectrophotometrically. The reaction proceeds according to the mechanism of vinylic substitution with a charge-transfer complex as the intermediate compound. the final product is a disubstituted quinone. The reaction mechanism is discussed.
Kinetics of the reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with tribenzylamine in acetonitrile has been measured spectrophotometrically. The product of this reaction is a stable anion radical of DDQ. The reaction is relatively slow, due to a considerable steric hindrance in both quinone and amine molecule. Activation parameters indicate a charge separation in the transition state. The mechanism of the reaction has been proposed.
Nucleophilic vinylic substitution of 2,3,5,6-tetrachloro-1,4-benzoquinone by imidazole in acetonitrile and benzene has been studied spectrophotometrically. The reaction product is the diaminodichlorosubstituted quinone. The values of the activation parameters indicate that there is a considerable charge separation in the transition state. The reaction mechanism is discussed.
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