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化学学报
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化学学报 ›› 1990, Vol. 48 ›› Issue (4): 382-387. 上一篇    下一篇

研究论文

反式-4-取代-2-氮杂金刚烷高氯酸盐的合成和立体化学

王广义;Grob, C.A   

  1. 巴塞尔大学有机化学研究所
  • 发布日期:1990-04-15

Syntheses and stereochemistry of hydroperchlorates of anti-4-substituted 2-azaadamantanes

WANG ANYI;Grob, C.A   

  • Published:1990-04-15

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本文报告了若干反式和顺式N-苯甲基-4-取代-2-氮杂金刚烷的合成, 取代基为:H, CH2OH, CH2OAc, CH2OTs, CO2CH3, OH, CONH2, OAc, Cl和CN。反式游离胺用高氯酸处理得N-苯甲基高氯酸盐, 后者催化氢解产生反式4-取代-2-氮杂金刚烷高氯酸盐, 游离胺的立体化学是根据红外和核磁共振光谱方法测定的。

关键词: 铵化合物, 催化, 红外分光光度法, 甲苯, 氮杂环化合物, 游离基, 核磁共振, 异构体, 立体化学, 高氯酸盐

N-Benzyl-anti and syn-4-substituted 2-azaadamantanes were prepared starting from adamantane I. Treatment of anti free amines with perchloric acid gave N-benzyl hydroperchlorates, which were hydrogenolyzed to provide the title compounds II (R = H, OH, Cl, cyano, CO2Me, CH2OH, etc.). Stereochem. of the free amines was determine with the help of IR and 1H NMR spectra.

Key words: AMMONIUM COMPOUND, CATALYSIS, INFRARED SPECTROPHOTOMETRY, METHYLBENZENE, NITROGEN HETEROCYCLICS, FREE RADICAL, NUCLEAR MAGNETIC RESONANCE, ISOMER, STEREOCHEMISTRY, PERCHLORATE

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