88691-17-2Relevant academic research and scientific papers
INTERACTION OF SULFENYL CHLORIDES WITH UNSATURATED ORGANOPHOSPHORUS COMPOUNDS: AdE3 REACTION MECHANISM AND REGIOCHEMISTRY OF ADDITION
Kutyrev, G. A.,Kapura, A. A.,Karataeva, F. Kh.,Cherkasov, R. A.,Samitov, Yu. Yu.,Pudovik, A. N.
, p. 345 - 360 (2007/10/02)
As evidenced by (1)H, (31)P, and (13)C NMR spectroscopy, phenylsulfenyl chloride, like phosphonosulfenyl chloride, adds to vinylphosphonates to produce a mixture of two regioisomers.Thermodynamic stability of β-chloroadducts is greater than that of α-chloroisomers.The 1,2-addition of C6H5SCl to isopropenyl- and styrylphosphonates and unsaturated thionophosphoryl compounds is regiospecific.Kinetic studies have established that the reactions might proceed by the AdE3-mechanism involving two molecules of an unsaturated reagent.The substituents at phosphorus and the carbon-carbon double bond in phosphonates affect the structure of the transition state in the limiting stage of the reaction, as does the medium.The effect of the organophosphorus group in the unsaturated reagent and sulfenyl chloride on the mechanism of the AdE-process has been analyzed.
