ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Acylation of Heterocycles with Carbonic Acid Derivatives. IV. Reaction of Benzoxazolin-2-thione with Aryl Cyanates. Kinetics and MechanismThe arylcyanate benzoxazoline-2-thione (1) reaction in the presence and absence of the tertiary amines yields 1-aryloxyiminocarbonylbenzoxazoline-2-thione (2) and 2-thiocyanatobenzoxazole (4). A mechanism is proposed based on the influences of the reactants concentration, the concentration and basicity of tertiary amines, the solvent-water concentration, the arylcyanate substituents electronic effects on the reaction rate and the apparent activation parameters. This mechanism consists in the nucleophilic attack of the benzoxazoline-2-thione S-atom on the cyanate, followed by rearrangement through a four-center transition state.
Additional Material:
8 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19843260118
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