2002organo-phosphorus compounds organo-phosphorus compounds S 0080
-162Intramolecular Cyclization of ω-Haloalkyl-Substituted Thiophosphorylacetonitriles:Synthesis and Stereochemistry of 3-Cyano-2-oxo-1,2-thiaphosphacyclanes.-Intramolecular S-alkylation of ω-haloalkyl-substituted thiophosphorylacetonitriles (III) and (XI) provides access to cyanooxothiaphospholanes and -thiaphosphinanes in low to moderate diastereoselectivity. The yields and diastereoselectivities are determined by substitution pattern of the starting acetonitriles as well as by the cyclization conditions. Diarylthiophosphinylacetonitriles like (VI) provide stable ω-iodoalkyl analogues [cf. (VII)] under the reaction conditions, which cyclize only very slowly. Higher thiaphosphacycles (7-membered rings) are not achieved under the reaction conditions. -(ODINETS, IRENE L.; VINOGRADOVA, NATALYA M.; LYSSENKO, KONSTANTIN A.; ANTIPIN, MICHAIL YU.; PETROVSKII, PAVEL V.; MASTRYUKOVA, TATYANA A.; Heteroat. Chem.