PHOTOINDUCED REACTIONS .25. A ZWITTERIONIC PEROXIDE INTERMEDIATE IN PHOTOSENSITIZED OXYGENATION OF FULLY N-ALKYLATED URIC ACIDS

被引：22

作者：

MATSUURA, T

SAITO, I

机构：

[1] Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, Kyoto

来源：

TETRAHEDRON | 1969年 / 25卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(01)83265-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photosensitized oxygenation of 1,3,7,9-tetramethyluric acid (7a) in methanol containing rose bengal as sensitizer yielded 4,5-dimethoxy-1,3,7,9-tetramethyluric acid (10) as the major product besides a small amount ofallocaffeic acid (11). When photosensitized oxygenation was carried out in chloroform in the presence ofmethylene blue, 7a gave 1,3,7-trimethylcaffolide (12a) and 1,3-dimethylparabanic acid (13). Under the same conditions, 1-ethyl-3,7,9-trimethyluric acid (7b) afforded 12b, 13, and 14b and 9-ethyl-1,3,7-trimethyluric arid (7c) gave 12c and 14c. Mechanisms involving an initial attack of singlet oxygen to 7 forming a zwitterionic peroxide are proposed. © 1969.

引用

页码：549 / &

共 30 条

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