Base Information
- Chemical Name:S-allyl S-methyl dithiocarbonate
- CAS No.:40515-45-5
- Molecular Formula:C5H8OS2
- Molecular Weight:148.25
- Hs Code.:
Synonyms:S-allyl S-methyl dithiocarbonate
Synonyms:S-allyl S-methyl dithiocarbonate
The research investigates the retro-ene type fragmentation of allylic dithiolcarbonates. The study found that the formation of 2-alkenyl alkyl sulfides from S-(2-alkenyl) S-alkyl dithiocarbonates, with the extrusion of COS, is effectively catalyzed by Lewis acids. Phenolic compounds, such as p-nitrophenol, also showed catalytic activity, promoting the reaction through an SNi'-type mechanism involving the attack of the alkylthio group on the β-carbon atom of the allylic system, with simultaneous double bond shift and COS elimination. The use of aluminum catalysts, like AlCl3 and Me2AlCl, resulted in significant rate enhancements, with the reaction proceeding smoothly at room temperature to yield sulfides in high quantities. The research also involved molecular orbital calculations on a model reaction pathway of S-allyl S-methyl dithiocarbonate (2A) to establish the reaction mechanism. The calculations indicated that the reaction barrier was lowered in the presence of AlCl3 and that the nature of the concerted reaction mechanism remained unchanged. The study demonstrated that the fragmentation reaction of allylic dithiolcarbonates falls into the category of retro-ene type reaction, a thermally allowed pericyclic reaction proceeding through a six-membered nonionic cyclic transition state.
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