2-Phenylalkanenitriles 1 react under PTC conditions with 1,1-or cis-dichloroethylene giving ethynylated products 2. Nitriles 1, α-substituted desoxybenzoines 6, 2-substituted phenylacetaldehydes 8, 1,3-dialkylindene 10 and substituted diethylmalonates 12 afford with trichloroethylene 1,2-dichlorovinylated derivatives, respectively 3, 7, enol ethers 9, 11 and 13. PTC reaction of trans-dichloroethylene with 1 or 10 lead to formation of 2-chlorovinylated 14 or ethynylated 16 products, respectively. In majority of cases the products were formed in good yield. The course of these reactions is rationalized.