Nitration of 2-Cyclohexenone Derivatives and Some Reactions of the Products

  • MATOBA KATSUHIDE
    Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
  • MORITA TAKASHI
    Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
  • YAMAZAKI TAKAO
    Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University

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Abstract

5,5-Dimethyl-2-cyclohexenone (Ia) and isophorone (Ib) were nitrated with isoamyl nitrate using potassium metal in liquid ammonia to give 5,5-dimethyl-2-nitro-1,3-cyclohexadienol (III) and 3,5,5-trimethyl-2-nitro-2-cyclohexenone (IVb), respectively. Compound III was treated with diazomethane to give an oxime (VI) and an intermediate to VI (V). Compound VI was derived to 2-methoxy-4,4-dimethyl-2,5-cyclohexadienone (IX) via the nitrone (VIII) and then the hydroxydienone (IIb). On the other hand, the reduction of IVb with sodium borohydride (SBH) was examined. The products were two epimeric nitro alcohols (Xa and XIa), a nitroketone (XII), and a nitro ester (XIII). Compound XIa was converted to Xa by using SBH or aqueous sodium hydroxide. Although the compound with axial acetate (XIc) was deacetoxylated under SBH reduction conditions, that with equatorial acetate (Xc) was inert to this reduction.

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