PHOTOCHEMISTRY OF BENZOPHENONE-CAPPED BETA-CYCLODEXTRIN

被引：11

作者：

BERGER, KL ^{[1
]}

NEMECEK, AL ^{[1
]}

ABELT, CJ ^{[1
]}

机构：

[1] COLL WILLIAM & MARY,DEPT CHEM,WILLIAMSBURG,VA 23185

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 11期

关键词：

D O I：

10.1021/jo00011a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photochemistry of 6A,6C-(3,3'-benzophenonedisulfonyl)-beta-cyclodextrin (1) is explored. Irradiation of 1 in H2O or aqueous CH3CN results in regioselective oxidation of a glucose C6 hydroxymethyl group, giving 2a and 2b via intramolecular H-abstraction by the excited benzophenone group. Molecular mechanics calculations suggest that the photooxidation occurs at the E and F glucose residues. In contrast, irradiation of 1 in aqueous i-PrOH gives rise to pinacol coupling products 3a-c.

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页码：3514 / 3520

页数：7

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