ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In contrast to many previous investigations, reaction conditions were found under which the nitration of durene (nitrating ratio of 1:1) gives predominantly, and in high yield, mononitrodurene rather than the usually formed dinitrodurene (plus unreacted durene). The method consists in nitrating by nitronium phosphorohexafluoride in nitromethane as solvent in presence of two equivalents of water.With mixed acid (HNO3 + H2SO4) in nitromethane and in acetonitrile durene forms also monoand no dinitrodurene; but under most conditions by-products are formed. Some of the by-products were identified.Some preliminary mechanistic results are reported: An addition complex of unknown structure is formed rapidly; 3, 6-dideuterodurene + D2O do not show a hydrogen isotope effect; the preferential formation of dinitrodurene under conventional conditions is due to the fact that the reaction occurs at encounter-controlled rate.
Additional Material:
8 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19690520615
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