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有机化学
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有机化学 ›› 1990, Vol. 10 ›› Issue (4): 360-365. 上一篇    下一篇

研究论文

水杨叉间溴缩苯胺的光发色和热消色反应过渡态

吴国生;葛明娟;林光灿;李尊良;舒菊坪   

  1. 中国科学院上海有机化学研究所;中国科学院上海光学精密机械研究所
  • 发布日期:1990-08-25

Transitions in the photocolouration and thermodecolouration of salicylaldehyde m-bromoanil

WU GUOSHENG;GE MINGJUAN;LIN GUANGCAN;LI ZUNLIANG;SHU JUPING   

  • Published:1990-08-25

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580

本文报道水杨叉间溴缩苯胺(1)的光致色变和热消色, 首次提出了它的光发色和热消色反应过渡态结构, 确认顺-反-反烯醇式水杨叉间溴缩苯胺(2)有光致色变性能, 而顺-顺-反式异构体则无此性能。选择1作为确定研究对象的另一个原因是由于激发态间位效应[9]的考虑, 1的氮原子将呈现更强的碱性, 降低热消色反应速率常数, 期望在较高的温度下观察到光致色变。

关键词: 苯甲醛 P, 光致变色, 反应机理, 溴化合物, 苯胺, 结构与性能关系, 水杨酰苯胺, 过渡态

In nonpolar solvent, salicylaldehyde m-bromoanil exists in 2 substable enol forms, cis-trans-trans (I) and cis-cis-trans (II), resp. Observation of the photocoloration stems from the formation of the trans-keto anil from I upon irradiation of its solution in petroleum ether at -170? It is most likely that the photoisomerization proceeds via an antarafacial 1,5-H-migrated Moebius array, while suprafacially 1,5-H-migrated Hueckel cycle of the cis-keto anil results in the formation of the photoinert II.

Key words: REACTION MECHANISM, BENZALDEHYDE P, BROMINE COMPOUNDS, PHOTOCHROMISM, ANILINE, STRUCTURE AND PROPERTY CORRELATION, SALICYLANILIDUM, TRANSITION STATE

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