Mass spectrometry and quantum chemical studies of the reaction of divinyl telluride with secondary phosphine sulfides: Synthesis of adducts

Abstract

Mass spectrometry and quantum chemical studies of the reaction of divinyl telluride with diphenylphosphine sulfide have been carried out. Reaction proceeds under radical initiation (AIBN, 63–68 °С, 2.5 h, THF, reactants molar ratio = 1:1) to afford the anti-Markovnikov monoadduct 1 and diadduct 2 in 67 and 23% yield, respectively. The former easily decomposes to give vinyldiphenylphosphine sulfide 3 (in 63% yield), ethylene and elemental tellurium, the structure of which represents mainly nano-sized powder consisting of agglomerates with average size of 350–450 nm. The comparative analysis of electron ionization mass spectra of compounds 1, 2 and 3 indicates that the presence of tellurium atom in adducts 1 and 2 reduces stability of their molecular ions and hinders the elimination of sulfur atom. Under conditions of chemical ionization of phosphine sulfides 1 and 3, the process of their protonation with CH5+ followed by the elimination of sulfur atom from [НМ]+ ion is dominant. These data are also confirmed by the results of quantum chemical calculations of the most stable protonated structures of phosphine sulfides 1 and 3.