ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The kinetics of the reactions of 1-chloro-, 1-fluoro- and 1-phenoxy-2,4-dinitrobenzene with piperidine, n-butylamine and benzylamine, and in the case of the ether, morpholine were studied as functions of nucleophile, DABCO and pyridine concentrations in tetrahydrofuran and ethyl acetate. The reactions of the ether with n-butylamine and benzylamine in benzene were also studied as functions of nucleophile, DABCO and pyridine concentrations. A comparison with results in the literature indicated that the reactions in tetrahydrofuran and ethyl acetate resemble those in dipolar aprotic solvents when primary amines are the nucleophiles and those in aprotic solvents when the nucleophile is a secondary amine. An explanation is suggested for the observation that whereas the reactions of 1-phenoxy-2,4-dinitrobenzene with piperidine and morpholine in both tetrahydrofuran and ethyl acetate are strongly catalysed by the nucleophiles, they are not catalysed by pyridine and there is either extremely weak or no catalysis by DABCO.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610030109
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