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Synthesis of 1,3,5,5‐tetranitrohexahydropyrimidine
Author(s) -
Levins D. A.,
Bedford C. D.,
Staats S. J.
Publication year - 1983
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.830080304
Subject(s) - chemistry , alkyl , amide , amine gas treating , nitric acid , medicinal chemistry , nitrosamine , ring (chemistry) , tertiary amine , organic chemistry , carcinogen
1,3,5,5‐Tetranitrohexahydropyrimidine, ( 1 ), was synthesized by the oxidative nitrolysis of 1,3‐diisopropyl‐5,5‐dinitrohexahydropyrimidine, (2), with 90% nitric acid. The course of the reaction was influenced by both the n‐alkyl substituents and the nitrolyzing medium. Compound 1 was synthesized by nitrolysis of N,N‐diisopropyl or dicyclohexyl substituents, while dimethyl, diethyl, or other di‐n‐alkyl substituents yielded ring‐cleaved products 3 and/or 4 . Similar effects were observed by varying the nitric acid concentration. The formation of nitramine products, rather than nitrosamine or alkyl amide products that generally result from tertiary amine nitrolysis, is attributed to conformational changes in a postulated nitronium ion‐amine complex intermediate.