58114-26-4Relevant academic research and scientific papers
EFFECT OF THE STRUCTURE OF THE SUBSTRATE AND NUCLEOPHILE ON THE REACTION RATES OF ARYLSULFONYLVINYLTRIALKYLAMMONIUM SALTS WITH AMINES
Popov, A. F.,Kravchenko, V. V.,Kostenko, L. I.,Kotenko, A. A.,Kovach, N. A.
, p. 1915 - 1917 (2007/10/02)
The kinetics of the reactions of arylsulfonylvinyltrialkylammonium salts with primary and secondary aliphatic amines in acetonitrile at 25 deg C were studied.On the basis of the low sensitivity of the reaction of β-(p-nitrophenylsulfonyl)vinyltriethylammonium chloride with alkylamines to the effect of the electronic and steric factors in the structure of the amines it was concluded that the transition state of the process is "looser" than in the reactions of the analogous substrates with a halogen as leaving group.The effect of the structure of the leaving trialkylammonium group on the rate of its substitution by the amino group was studied for the reaction of β-(p-nitrophenylsulfonyl)vinyltrialkylammonium chlorides with piperidine.The obtained data indicate that the process take place by an addition-elimination mechanism.
