Accession Number : ADA141825

Title :   Nitrolysis of the CN Single Bond and Related Chemistry of Nitro and Nitroso Groups.

Descriptive Note : Annual rept. 1 Jan-31 Dec 83,

Corporate Author : ILLINOIS UNIV AT CHICAGO CIRCLE

Personal Author(s) : Boyer,J H

PDF Url : ADA141825

Report Date : Mar 1984

Pagination or Media Count : 35

Abstract : Nitric acid in acetic anhydride converted N,N-dimethyl-benzylamine 1 to N-methyl-N-nitrosobenzylamine 2 (76%) and benzaldehyde. Six additional acyclic and alicyclic tertiary amines similarly gave nitrosamines; 1,4-diazabicyclo 2,2,2 octane gave an intractable mixture. An explanation for the conversions is discussed. Addition of hydrocloric acid to the reaction mixture led to recovery of the amine 1 (36%), and to its conversion (54%) to the nitrosamine 2 without the detectable formation of benzaldehyde; in contrast nitric acid (100%) and anhydrous hydrogen chloride in acetic anhydride converted the amine 1 to benzaldehyde (69%) and to the nitrosamine 2 in low yield. Nitrosamine 2 and N-methyl-N-nitroso-Beta-phenethylamine 3 were oxidized to nitramines 4 and 5. It became desirable to incorporate alpha-functions into nitrosamines to provide schemes for the preparation of cage structure high energy materials. A proposed scheme is shown.

Descriptors :   *Nitrogen compounds, *Chemical reactions, *Nitrosamines, Nitric acid, Nitroso compounds, Synthesis(Chemistry), High energy, Hydrogen chloride, Explosives

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE