Kinetics and mechanism of the reaction of 4-nitrobenzylidene dichloride with hydroxide ion

Abstract

The reaction of 4-nitrobenzy idene dichloride with hydroxide ion in aqueous alcoholic solvents under nitrogen gives mainly dimeric type products, viz. tetrachloro-1,2-bis-(p-nitrophenyl)ethane, αα′-dichloro-4,4′-dinitrostilbenes and bis-(4-nitrophenyl)acetylene, and also a significant amount of 4-nitrobenzyl chloride. Kinetic evidence indicates that the reaction is second order with respect to 4-nitrobenzylidene dichloride. These results support an electron transfer or radical mechanism and rule out rate-determining free carbanion or carbene formation pathways.