RESEARCH IN FLUORO-NITRO COMPOUNDS
Abstract
The conversion of carbonyl groups to gem-difluoramines using difluoramine and H2SO4, has been extended to polynitroketones, gamma-diketones, and ketoesters. The addition of difluoramine to simple unbranched olefins was accomplished using H2SO4, methanesulfonic acid, or BF3-H3PO4 complex as the catalyst. The latter catalyst was also applied to the addition of difluoramine to an acetylene. Aqueous fluorination of amides and carbamates, resulting in the displacement of H or CO groups on N by F, was extended to a series of difunctional and cyclic substrates. The acidcatalyzed reaction of ethyl N-fluorocarbamate with aldehydes gave simple addition and replacement of the resulting hydroxyl group. This carbamate also added to olefins. It reacted with H2SO4 to give the N-fluoroammonium salt. The nitration of N-fluoro-N-n-butylcarbamate gave N-fluoro-N-nitro-n-butylamine. Gamma-difluoraminobutyric acid was converted by the Curtius reaction sequence to the isocyanate. A gemdifluoramine was reduced with LiAlH to the monoamine. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 01, 1962
- Accession Number
- AD0332447
Entities
People
- K. Baum
- V. Grakauskas
Organizations
- Aerojet Rocketdyne Holdings