55975-44-5Relevant academic research and scientific papers
Hexabromoacetone as tribromoacetylating agent of alcohols and amines and as mediator in the conversion of carboxylic acids into amides in the presence of triphenylphosphine
Menezes, Fabrício G.,Kolling, Rosane,Bortoluzzi, Adaílton J.,Gallardo, Hugo,Zucco, César
, p. 2559 - 2561 (2009)
Hexabromoacetone has been used as an alternative tribromoacetylating agent of primary alcohols and amines and as mediator in the conversion of carboxylic acids into amides in the presence of triphenylphosphine. The reactions have been performed under mild conditions with moderate to good yields. All the products have been adequately characterized by their physical and spectroscopic properties.
TRANSITION THROUGH AN ISOPARAMETRIC POINT RELATIVE TO SUBSTITUENT IN THE REACTION OF AROYL BROMIDES WITH PRIMARY ARYLAMINES. RELATIONSHIP BETWEEN REACTIVITY AND SELECTIVITY
Shpan'ko, I. V.,Goncharev, A. N.,Chetverova, E. V.,Likhomanenko, E. E.
, p. 1290 - 1295 (2007/10/02)
Rates were measured for the reactions of aroyl bromides with primary arylamines in 1:1 chlorobenzene-cyclohexane at 25 deg C.The kinetic data were treated by the Hammett-Taft equations and cross correlation.This is the first reported transition through an isoparametric point relative to the structure of the nucleophile accompanied by inversion of the sign of the sensitivity parameter relative to the substrate structure in the aroyl bromide-primary arylamine reaction system.The results of the cross correlation analysis were interpreted on the basis of a concerted mechanism involving nucleophilic substitution at the carbonyl carbon atom.The relationship between the reactivity of the system studied and its selectivity was examined.
EFFECTS OF LEAVING GROUPS IN ACYL TRANSFER REACTIONS CATALYZED BY ORGANIC BASES
Titskii, G. D.,Turovskaya, M. K.
, p. 1911 - 1914 (2007/10/02)
In the benzoylation reactions of aromatic amines, catalyzed by organic bases, substitution of the chlorine atom by bromine in the substrate leads to an increase in the reactivity.The element effect of the leaving group (halogen) decreases with increase in the activity of the basic catalyst.Substitution of the hydrogen atoms at the nitrogen in the arylamine by deuterium leads to the appearance of a secondary isotope effect.
QUANTITATIVE RELATIONSHIPS IN THE REACTIONS OF BENZOYL CHLORIDE WITH ARYLAMINES IN THE PRESENCE OF TETRABUTYLAMMONIUM CHLORIDE IN BENZENE
Turovskaya, M. K.,Titskii, G. D.,Litvinenko, L. M.,Zamashchikov, V. V.
, p. 1874 - 1878 (2007/10/02)
The kinetics of the reactions of benzoyl chloride with 4-nitroaniline and 3,5-dinitro-4-chloroaniline in the presence of tetrabutylammonium chloride in benzene at 25 deg C were studied.It was found that an active associate, formed from the arylamine and the catalyst through a hydrogen bond, accumulates.The equilibrium constants for the formation of the active associate and its reactivity in relation to the acylating agent were determined.A stage mechanism of catalysis with the participation of ammonium ion pairs is examined for the reaction.
