Bulletin of the Korean Chemical Society

  • 제7권3호
  • /
  • Pages.201-204
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  • 1986
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Reduction of N-Arylpyridinium Compounds by Sodium Borohydride and Dithionite: Regioselectivity and Isomerization of Reduction Products

  • 발행 : 1986.06.20
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초록

Reduction of N-arylpyridinium compounds by $NaBH_4$ gave mixtures of the corresponding 1,2-dihydropyridine(major) and 1,4-dihydropyridine(minor), whereas similar reduction by $Na_2S_2O_4$ produced 1,4-dihydropyridines regioselectively. The proportion of 1,4-isomer in the product by $NaBH_4$ reduction appeared to increase with the electron-donating ability of N-aryl groups. When the N-aryl group is p-methylphenyl, p-ethylphenyl or p-methoxyphenyl, the 1,2-dihydropyridines in ethanol-water (4:1) solutions isomerized to the corresponding 1,4-dihydropyridines. N-(p-methylphenyl)-1,2-dihydropyridine and N-(p-ethylphenyl)-1,2-dihydropyridine in solid state also isomerized to the corresponding 1,4-dihydropyridines. The different behaviors of reduction among N-arylpyridiniums and isomerization of the reduction products depending on the substituent in N-aryl group were explained in terms of difference in the electronic effects of the substituents.

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참고문헌

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피인용 문헌

  1. STUDIES ON THE OXIDATION OF 1,4-DISUBSTITUTED-1,2,3,6-TETRAHYDROPYRIDINES vol.34, pp.3, 1986, https://doi.org/10.1081/dmr-120005655
  2. Dramatic HER Suppression on Ag Electrodes via Molecular Films for Highly Selective CO2 to CO Reduction vol.11, pp.None, 1986, https://doi.org/10.1021/acscatal.1c00338