67800-07-1Relevant articles and documents
KINETICS OF THE SOLVOLYTIC DEHYDROHALOGENATION OF 3,5-DICHLORO-2,4,6-TRIMETHYLBENZOHYDROXIMOYL CHLORIDE AND BROMIDE IN METHANOL
Beltrame, Paolo,Carniti, Paolo,Gelli, Gioanna,Loi, Aldo
, p. 603 - 608 (2007/10/02)
The title reactions were found to proceed smoothly to an equilibrium, producing 3,5-dichloro-2,4,6-trimethylbenzonitrile oxide.The reverse reactions were also carried out.Equilibrium constants were determined in the range from 20 to 50 deg C for the chloride and from 10 to 30 deg C for the bromide.Kinetics were studied at the same temperatures with excess acid and halide concentrations, measuring pseudo-first-order rate coefficients.Results were interpreted using a two-step kinetic model with a rapid acid ionisation of the hydroximoyl halide followed by a slower cleavage of the carbon-halogen bond.In the experimental conditions, the addition of methanol to the nitrile oxide, under acid catalysis, was found to be too slow to affect the main reactions.