Abstract
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. Copyright © 1969 Verlag GmbH & Co. KGaA, Weinheim
Recommended Citation
S. B. Hanna et al., "Das Problem Der Mononitrierung Von Durol," Helvetica Chimica Acta, vol. 52, no. 6, pp. 1537 - 1548, Wiley, Jan 1969.
The definitive version is available at https://doi.org/10.1002/hlca.19690520615
Department(s)
Chemistry
Publication Status
Full Access
International Standard Serial Number (ISSN)
1522-2675; 0018-019X
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2026 Wiley, All rights reserved.
Publication Date
01 Jan 1969
