The cyclic voltammetry and cathodic reduction of steroidal homoallylic nitro esters. Dimerization vs. cyclopropane formation.

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概要

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• The cathodic reduction of homoallylic nitro esters was carried out in DMF–TBAP using platinum electrodes. The reaction was found to be highly dependent on the ester-leaving group: Whereas 6-nitrocholest-5-en-3β-yl acetate (<B>3a</B>) gave a 3,3′-dimer <B>4</B>, 3β-tosylate <B>3d</B> gave a cyclosteroid, 6β-nitro-3α,5-cyclo-5α-cholestane (<B>7</B>). 3β-Trifluoroacetate showed intermediate behavior and gave both <B>4</B> and <B>7</B>. Similarly, 6-nitrocholest-5-ene-3β,19-diol 3-acetate 19-tosylate gave 5β,19-cyclosteroid. The cyclic voltammetry was carried out for these and related compounds. A reversible cyclic voltammogram was recorded for <B>3a</B>, but <B>3d</B> showed no anodic peak on potential reversal. A possible electron-transfer and the following chemical-reaction mechanism was discussed.

• 公益社団法人 日本化学会の論文

著者

• Sato Takeo

  Department Of Allergy And Immunological Diseases Tokyo Metropolitan Komagome Hospital

• Kobayashi Shoichi

  Department of Chemistry, Tokyo Metropolitan University

• KOBAYASHI Shoichi

  Department of Agro-bioscience, Iwate University

• Komeichi Yoshihisa

  Department of Chemistry, Tokyo Metropolitan University

• Omura Aira

  Department of Chemistry, Tokyo Metropolitan University

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