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Reduction of N-Arylpyridinium Compounds by Sodium Borohydride and Dithionite: Regioselectivity and Isomerization of Reduction Products
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  • Reduction of N-Arylpyridinium Compounds by Sodium Borohydride and Dithionite: Regioselectivity and Isomerization of Reduction Products
  • Reduction of N-Arylpyridinium Compounds by Sodium Borohydride and Dithionite: Regioselectivity and Isomerization of Reduction Products
저자명
Koh Park. Kwang-Hee,Han. Du-Hee,Shin. Dae-Hyun
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1986년|7권 3호|pp.201-204 (4 pages)
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대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

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.