SOME DEOXYGENATION REACTIONS OF AMINE OXIDES.
Abstract
This project involves a survey of the reactions of amine oxides with various electrophilic compounds such as anhydrides, esters, alpha, betaunsaturated carbonyl compounds and epoxides. A new oxidation of epoxides by amine oxides or dimethyl sulfoxide was discovered. The reactions of pyridine-N-oxide with dimethyl acetylenedicarboxylate and with naphthoquinone result in self-reactions of the latter compounds. PyridineN-oxide was found to form a 2:1 molecular complex, presumably of the charge-transfer variety with tetrahydroxydinaphthalene. The structure of the ''hydrazone'' of dehydrodinaphthoquinone was reinvestigated. An unusual redox reaction occured when N-acyloxypyridinium halides were pyrolyzed producing pyridine, the carboxylic acid and halogenated organics. Other reactions discussed include: (1) reaction of phenyl acetate with 2- and 4-picoline-N-oxide; (2) phenylacetic anhydride treated with 2- and 4-picolineN-oxide; (3) oxidative decarboxylation of some carboxylic acids by pyridine-N-oxide. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Aug 28, 1963
- Accession Number
- AD0419928
Entities
People
- Theodore A Cohen
Organizations
- University of Pittsburgh