RESEARCH IN FLUORO-NITRO COMPOUNDS.
Abstract
Reactions of diazonium salts with N-fluorocarbamates in the presence of mild bases gave azides and alkyl fluoroformate. Reactions of diazonium salts with difluoramine gave aromatic azides with fluorine introduced into the ortho or para position. The reaction 2,5,8-triketononane with difluoramine and fuming sulfuric acid gave 2-methyl-2,5-bis(difluoramino)-5-(gamma, gamma-bis(difluoramino)butyl) tetrahydrofuran. No reaction took place between picryl chloride and neat liquid difluoramine in 73 hours. The addition of pyridine gave no fluorine-containing products. The reaction ethyl diazoacetate with difluoramine and sulfuric acid gave ethyl difluoroaminoacetate. Ethyl azodicarboxylate did not react with difluoramine, and nitroacetaldehyde phenylhydrazone gave only tars. 2-Phenylazo-2-nitropropane was converted to 2-phenylazo-2-difluoraminopropane. A simplified process for the preparation of high-purity fluoroammonium perchlorate (SAP) was developed, based on the reaction between isopropyl N-fluorocarbamate and anhydrous perchloric acid. Yields were almost quantitative. Alkylation and Mannich condensation reactions of 2,2-dinitro-2-fluoroethanol were briefly investigated. 2,2-Dinitro-2-fluoroethyl methyl and 2,2-dinitro-2-fluoroethyl allyl ethers were obtained on treatment of alkaline solutions of 2,2-dinitro-2-fluoroethanol with dimethyl sulfate and allyl bromide, respectively.
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 01, 1966
- Accession Number
- AD0380457
Entities
People
- K. Baum
- L. A. Maucieri
- V. Grakauskas
Organizations
- Aerojet Rocketdyne Holdings