
%0 Journal Article
%A McLennan, DJ 
%T The reaction of 1,1-Dichloro-2,2-di(p-chlorophenyl)ethane (DDD) with sodium thiophenoxide in ethanol
%J Australian Journal of Chemistry
%D 1969/09/01
%V 22
%N 9
%P 1905-1913
%K 
%R https://doi.org/10.1071/CH9691905
%U https://www.publish.csiro.au/paper/CH9691905 
%X The reaction of 1,1-dichloro-2,2-di(p-chlorophenyl)ethane (DDD) with sodium thiophenoxide in ethanol yields the unexpected product Ar2C=CHSPh (Ar = p-ClC6H4) by a second-order process. Elimination-addition- decomposition; elimination-substitution; and direct disubstitution- decomposition mechanisms have been considered. The absence of a &#946;- deuterium isotope effect in the reaction (contrasted with kH/kD = 4.6 for the E2 elimination using sodium ethoxide as the base) argues for direct SN2 substitution of both aliphatic chlorines of DDD followed by decomposition of Ar2CHCH(SPh)2 (which was not detected) to the observed product and thiophenol. 
