YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Studies on 7-Membered Ring Derivatives. I
Reaction of 4-Oxohomocamphor with Nitrous Acid
Ken'iti TakedaWataru Nagata
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1950 年 70 巻 7-8 号 p. 401-404

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Reaction of 4-oxohomocamphor with nitrous acid at a low temperature (0-5°) resulted, contrary to our expectations, in the formation of 3-nitro-4-oxohomocamphor, m.p. 128° as the chief product, and a small amount of 3-oximino-4-oxohomocamphor, m.p. 113°. As a result of investigating how nitration could occur with nitrous acid at such a low temperature, it was found that the oxygen in the air seemed to act catalytically in this reaction, and nitrous acid probably acted as a carrier of oxygen. Therefore, the same reaction was carried out in inactive gases (N2 or CO2) and oximino-compound was obtained as the main product. Both compounds were reduced catalytically, giving the same amine, 3-amino-4-oxohomocamphor, m.p. 228° (decomp.).

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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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