Formation of 4-hydroxy-3-(oxan-3-yl)coumarin from photochemical reaction between 4-hydroxycoumarin and 3,4-dihydro-2H-pyran and MO analysis

被引：5
|
作者：
Shimo, Tetsuro [1 ]
Sato, Kenya [1 ]
Wang, Weidong [1 ]
Obata, Toru [2 ]
Iwanaga, Tetsuo [3 ]
Shinmyozu, Teruo [3 ]
Somekawa, Kenichi [1 ]
机构：
[1] Kagoshima Univ, Dept Appl Chem & Chem Engn, Fac Engn, Kagoshima 8900065, Japan
[2] Kagoshima Prefectural Inst Ind Technol, Hayato, Kirishima 8905105, Japan
[3] Kyushu Univ, IMCE, Fukuoka 8128581, Japan
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2008年 / 81卷 / 07期
关键词：
D O I：
10.1246/bcsj.81.894
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Photochemical reaction of 4-hydroxycoumarin with 3,4-dihydro-2H-pyran gave 4-hydroxy-3-(oxan-3-yl)coumarin whose formation was explained by considering a hydrogen shift and Successive keto-enol isomerization from a head-tail biradical intermediate (A). The reaction mechanism was confirmed by molecular orbital analysis to he induced by intermolecular hydrogen bonding between the 4-OH and pyran oxygen at the transition state.
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收藏
页码：894 / 896
页数：3
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