Nitrolysis of the CN Single Bond and Related Chemistry of Nitro and Nitroso Groups
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-trioxo(2,2,2)bicyclooctane 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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 01, 1985
- Accession Number
- ADA151753
Entities
People
- J. H. Boyer
Organizations
- University of Illinois at Chicago