Reaction of diethylsilane with dialkenyl sulfides as a path for the synthesis of heterocyclic systems containing silicon and sulfur atoms

Abstract

1. The hydrosilylation of divinyl sulfide by diethylsilane, catalyzed by H2PtCl6 and (Ph3P)3RhCl, is accompanied by the hydrogenation and cyclization of the obtained monoadducts. The ratio of the reaction products depends on the amount and nature of the catalyst. 2. The reaction of diethylsilane with diallyl sulfide in the presence of Pt catalyst leads to the formation of a mixture of the Β- and θ-isomers. With Rh catalyst the reaction proceeds selectively in harmony with the Farmer rule. 3. The intramolecular hydrosilylation of the obtained monoadducts, containing Si-H and a double bond, in the presence of the indicated catalysts leads to compounds with either four-, five- or eight-membered rings, which contain Si and S atoms. (Ph3P)3RhCl is the more efficient cyclization catalyst. 4. The cyclization of the isomeric diethylvinylthioethylsilanes proceeds selectively as α-addition. Ring closure of the allylthiopropyl-substituted silane occurs at the terminal C atom of the double bond.