Tetrahedron p. 1679 - 1684 (1988)
Update date:2022-08-16
Topics:
Crampton, Michael R.
Jones, Michael
Scranage, John K.
Golding, Peter
Mechanistic studies of the nitration of hexamethylenetetramine (1) and some derivatives are reported and are compared with acetylation reactions.Nitration reactions, with nitric acid, were carried out using mixtures of <15N4>- and <14N4>-compounds and the destination of the nitrogen-isotopes in the products was determined mass spectrometrically.The results show that in nitration of (1) to give 3,7-dinitro-1,3,5,7-tetraazabicyclo<3.3.1>nonane (DPT) extensive ring cleavage occurs to give species containing single amino-nitrogen fragments.Howover the nitration of 3,7-diacetyl- 1,3,5,7-tetraazabicyclo<3.3.1>nonane
Doi:10.1134/S1070363219090214
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(2001)Doi:10.1016/S0020-1693(00)86744-4
(1985)Doi:10.1039/C39790000591
(1979)Doi:10.1007/BF02882393
(1950)