
TY  - JOUR
A1  - McLennan, DJ 
T1  - The reaction of 1,1-Dichloro-2,2-di(p-chlorophenyl)ethane (DDD) with sodium thiophenoxide in ethanol
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1969
VL  - 22
IS  - 9
SP  - 1905
EP  - 1913
KW  - 
UR  - https://doi.org/10.1071/CH9691905 
N2  - 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. 
ER  -

