SOME DEOXYGENATION REACTIONS OF AMINE OXIDES.
PITTSBURGH UNIV PA
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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 21 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