Accession Number:

ADA151753

Title:

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

Descriptive Note:

Annual rept. 1 Jan-31 Dec 1984

Corporate Author:

ILLINOIS UNIV AT CHICAGO CIRCLE

Personal Author(s):

Report Date:

1985-02-01

Pagination or Media Count:

63.0

Abstract:

For the efficient conversion of mono-tert-amines to nitrosamines treatment with dinitrogen tetroxide in an inert solvent at 0-45 has been developed. Attempts to oxidize the new R-salt carbinols A to RDX-ketones B have been unsuccessful. New attempts to achieve C-functionalization of RDX will be examined. Uncatalyzed debromination of nitrodibromoacetonitrile by treatment with tetramethylethylene, dimethyl sulfide, and triethylamine under mild conditions gave respectively 3-cyano-4,4,5,5-tetramethylisoxazol-2-ine-2-oxide, dimethylsulfonium cyanonitromethylide, and triethylammonium cyanonitromethylide. Base catalysed conversions SRN1 and related reactions of nitroacetonitrile and phenylnitroacetonitrile were examined. The known compounds 5,7-dioxo 2,2,2 bicyclooct-2-ene and 2,6,7-trioxo2,2,2bicyclooctane were prepared for investigations designed to provide nitro derivatives. Oxime derivatives have been prepared for conversion to nitro derivatives. Originator supplied keywords include Tert-amines, Nitrosamines, Nitramines, alpha-Substitution in nitrosamines, Nitrocyanocarbenes, SRNl and related reactions, Electron transfer, Barrelene derivatives.

Subject Categories:

  • Organic Chemistry
  • Ammunition and Explosives

Distribution Statement:

APPROVED FOR PUBLIC RELEASE