6533b7dcfe1ef96bd12727c3

RESEARCH PRODUCT

By-products in the rearrangement of N-methyl-N-phenylnitramine

Ewa NowakowskaZdzisław DaszkiewiczJanusz B. Kyzioł

subject

Nitrosobenzenechemistry.chemical_compoundAqueous solutionchemistryOrganic ChemistryDrug DiscoveryOrganic chemistryBiochemistryMedicinal chemistry

description

Abstract N-Methyl-N-phenylnitramine was rearranged in the aqueous dioxane — sulphuric acid mixture to 2-nitro- and 4-nitro-N-methylanilines. The isomer ratio was independent of the acidity within the range of −0.3 > Ho > −2.8. Some by-products were isolated and identified e.g. N-methyl-N-nitrosoaniline, its 2-nitro and 4-nitro derivatives, nitrosobenzene and 4′,4″-bis-(N-methylamino)-3′,3″-dinitrodiphenylmethane. The mechanism of the nitramine rearrangement is discussed.

https://doi.org/10.1016/s0040-4020(98)00279-8