ChemInform Abstract: Reactions of Dialkoxyphosphoryl and Phenylsulfenyl Chlorides, Dithiophosphoric Acids, and S‐Trimethylsilyl Dithiophosphates with p‐Vinylbenzyltrimethylstannane.

Abstract

The dithiophosphates (II) react with the vinylbenzylstannane (Ia) to give the anti‐Markovnikov adducts (III), whereas the reaction of (IIa) with 4‐methoxystyrene (IV) leads to the formation of the Markovnikov adduct (V).

Synthesis of Disulfides from the Palladium(0)-Catalyzed Reactions of Sulfenyl Halides and Organostannanes

“…Similarly, Quintard and co-workers reported a palladium-catalyzed coupling reaction between acyl chlorides and vinylstannanes to produce α,β-unsaturated ketones. Since the sulfur of the sulfonyl chloride and the carbon of the acyl halide exhibit similar electrophilic character in the displacement of the stannyl group from the vinylstannane, and since the sulfur of sulfenyl halides is electrophilic in cleavage reactions with vinylstannanes, we chose to determine whether vinyl sulfides could be obtained from the palladium-catalyzed coupling of sulfenyl chlorides and vinylstannanes. To the contrary, the palladium-catalyzed reaction between sulfenyl chlorides and vinylstannanes leads to high yields of the corresponding disulfide, a trialkytin chloride, and vinyl chloride.…”