Nitrophenylcarbenes. Part III. Kinetics of the decomposition of 4-nitrobenzyl chloride and dimethyl-4-nitrobenzylsulphonium ion in sodium hydroxide. A reinvestigation

Abstract

The reactions of 4-nitrobenzyl chloride and dimethyl-4-nitrobenzylsulphonium salt in sodium hydroxide solution both give high yields (66–74%) of 4,4′-dinitrostilbene. These reactions are sensitive to air or oxygen but when carried out under an atmosphere of nitrogen overall third-order kinetic behaviour was found; each reaction being first order in hydroxide ion and second order in the nitrobenzyl compound. The evidence presented shows that α-elimination is unlikely in these reactions but S_N2 or radical mechanisms are more likely.