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化学学报
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化学学报 ›› 1987, Vol. 45 ›› Issue (4): 340-343. 上一篇    下一篇

研究论文

分子内1,3-偶极环加成反应的研究II: 呋喃偶极体系的热及光化学反应

陈庆华;王学良   

  1. 北京师范大学化学系
  • 发布日期:1987-04-15

Studies on intramolecular 1,3-dipolar cycloaddition reactions II: The thermochemical and photochemical reactions of the furan 1,3-dipolar nitrone system

CHEN QINGHUA;WANG XUELIANG   

  • Published:1987-04-15

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494

被引次数

2

合成并研究了呋喃1,3-偶极C-2-呋喃-N-烯基硝酮(1)的热和光化学反应.1的热化学环加成反应具有区域选择性.生成氧氮杂二环辛烷类化合物.日光灯照明下加热还可得到双键迁移产物.1在波长>302nm下的光化反应产物是氧氮杂环丙烷,而在λ>270nm下除了还有重排产物N-戊烯基-2-呋喃甲酰胺,氧氮杂环丙烷不稳定,加热下通过1发生分子内环加成反应.

关键词: 光化学反应, 反应机理, 氮杂环化合物, 选择性, 呋喃 P, 重排反应, 肟, 环加成反应, 氧杂环化合物, 能级

The synthesis of 1,3-dipolar nitrone (I) and its thermochem. and photochem. reactions have been investigated. The intramol. cycloaddn. is regioselective and the cyclization products are II and III in roughly 2:1 ratio (total yield 80%). The thermochem. reaction under sunlamp light also produces the double bond migration product IV (18%). The photochem. reaction of I under irradiation at l ?02 nm gives oxaziridine V (78%), while under l ?70 nm the rearrangement product VI (15%) is obtained directly besides V (43%). Compound V is very reactive and undergoes an intramol. cycloaddn. reaction through I on heating.

Key words: PHOTOCHEMICAL REACTION, REACTION MECHANISM, NITROGEN HETEROCYCLICS, SELECTIVITY, FURAN P, REARRANGEMENT REACTION, OXIME, CYCLOADDITION REACTION, OXYGEN HETEROCYCLICS, ENERGY LEVELS

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