Nanosized particles of organically modified silica as microreactors to enhance the regioselectivity in the photocycloaddition of 9-substituted anthracenes

被引：21

作者：

Wu, DY ^{[1
]}

Chen, B ^{[1
]}

Fu, XG ^{[1
]}

Wu, LZ ^{[1
]}

Zhang, LP ^{[1
]}

Tung, CH ^{[1
]}

机构：

[1] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100101, Peoples R China

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 07期

关键词：

D O I：

10.1021/ol0341041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Nanosized particles of modified silica with 3-ammoniumpropyl residue have been prepared and successfully used as microreactors to control the regioselectivity of the photocycloaddition of five 9-substituted anthracences [AnCH(2)N(+)(CH3)(3)Br- (1), AnCH(2)COO(-)Na(+) (2), AnCH(2)CH(2)COOH (3), AnCH(2)OH (4), AnCH(3) (5), where An = 9-anthryl]. While the photocycloaddition of the five substrates in methanol mainly gave rise to their head-to-tall (h-t) photocyclomers, irradiation of 1-4 incorporated in the suspension of the modified silica in methanol almost exclusively yielded the head-to-head (h-h) photocyclomers with high quantum yields.

引用

页码：1075 / 1077

页数：3