ORGANIC DEUTERIUM COMPOUNDS: V. THE CHLORINATION OF PROPYNE AND PROPYNE-d4

Chlorination of propyne at 70 °C. gave 60 to 65% yields of 1,1,2,2-tetrachloropropane and 15 to 20% yields of trans-1,2-dichloro-1-propene. 1,1,2,2-Tetrachloropropane-d4 was similarly prepared from propyne-d4. Nearly theoretical yields of cis- and trans-1,2-dichloro-1-propene were obtained by partial dechlorination of tetrachloropropane. Deuterated cis- and trans-1,2-dichloro-1-propene were obtained in the same manner from 1,1,2,2-tetrachloropropane-d4.