Abstract p-Chlorothiophenol reacts with 1-methyl-1, 2, 5, 6-tetrahydropyridine-X-carbonitriles (1, X= 4, 6, X= 3) and with 1-methyl-1, Y-dihydropyridine-3-carbonitrile (7, Y= 6, 8, Y= 4) to give the anticipated addition products. Geometric isomers were formed from 6, but not from 1, and the stereochemistry of the products has been determined. The chemistry of the reactions with p-cresol was quite different. No reaction occurred with 6 or 7, while 8 gave a ...