SYNTHESIS AND PHOTOCHEMISTRY OF SOME ANTHRAQUINONE-SUBSTITUTED BETA-CYCLODEXTRINS

被引：49

作者：

AQUINO, AM ^{[1
]}

ABELT, CJ ^{[1
]}

BERGER, KL ^{[1
]}

DARRAGH, CM ^{[1
]}

KELLEY, SE ^{[1
]}

COSSETTE, MV ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 15期

关键词：

D O I：

10.1021/ja00171a022

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

Anthraquinone-substituted β-cyclodextrins (β-CD) 1-3 have been synthesized by reaction of the corresponding sulfonyl chlorides with β-CD. The anthraquinone-capped β-CD 3 is produced as a mixture of A, C and A, D isomers. Irradiation of 1-3 results in the formation of the corresponding hydroquinones and oxidation of the CD moiety. The main photoproduct from 2 after regeneration of the anthraquinone contains a C6 aldehyde in a hemiacetal or hydrate form. Molecular mechanics suggests that the position of the aldehyde is on the E-glucose ring and that the intramolecular H-abstraction reaction shows some selectivity. © 1990, American Chemical Society. All rights reserved.

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页码：5819 / 5824

页数：6

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