5330-96-1Relevant academic research and scientific papers
The common ion effect in sulfenylhalogenation of alkenes in formic acid
Skorobogatova,Shalin,Kartashov,Zefirov
, p. 90 - 95 (1997)
The reactions of 2,4-dinitrobenzenesulfenyl chloride with cyclohexene and allylbenzene in formic acid were studied. In this solvent, the reaction yields solvo-adducts and the products of addition of the reagent to the double bond. The reaction follows kinetics of the second order, first order with respect to each reagent. The hydrogen chloride evolved in the reaction has no effect on the overall rate of the process but sharply decreases the rate of accumulation of solvo-adducts due to the common ion effect. In the reaction with allylbenzene, the yield of the solvo-adduct can vary under the action of HCl from 88% at low degrees of reagent conversion to 30% when the reaction is complete.
DOPING-ADDITION OF ARENESULFENYL CHLORIDES TO OLEFINS IN THE PRESENCE OF PERCHLORIC ACID AND THE LITHIUM PERCHLORATE. CRITERIA OF LIMITING VARIANTS IN MECHANISM OF THESE REACTIONS
Kartashov, V. R.,Sorobogatova, E. V.,Grudzinskaya, E. Yu.,Zefirov, N. S.,Caple, R.
, p. 2231 - 2242 (2007/10/02)
The addition of perchloric acid in the addition reactions of sulfenyl chlorides to olefins gives rise to a doping effect, which exceeds the analogous effect of lithium perchlorate.Analysis of the dependence of rate of the model reactions and the yields of the doping products on the perchloric acid and lithium perchlorate concentrations showed that the doping additions can operate by two mechanisms, i.e., by the mechanism of a normal salt effect in the controlling state and by a mechanism of ion-pair exchange in the subsequent fast stages.
KINETICS AND DOPING EFFECT IN THE ADDITION OF 2,4-DINITROPHENYLSULFENYL CHLORIDE AND DITHIOCYANOGEN TO OLEFINS
Skorobogatova, E. V.,Grudzinskaya, E. Yu.,Afanas'ev, P. S,Kartashov, V. R.,Zefirov, N. S.,Caple, R.
, p. 1814 - 1822 (2007/10/02)
The rate of the doping addition in the reactions of 2,4-dinitrophenylsulfenyl chloride with cyclohexene an methylenecyclobutane and of dithiocyanogen with cyclohexene and substituted styrenes in the presence of lithium perchlorate is described by the normal salt effect equation.On the other hand, the rate of formation of the doping products may exceed or lag behind the increase in the total reaction rate.These results were interpreted in the framework of an ion-pair mechanism.
