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

Da-Yong Wu; Bin Chen; Xiao-Gang Fu; Li-Zhu Wu; Li-Ping Zhang; Chen-Ho Tung

doi:10.1021/ol0341041

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

Org Lett. 2003 Apr 3;5(7):1075-7. doi: 10.1021/ol0341041.

Authors

Da-Yong Wu¹, Bin Chen, Xiao-Gang Fu, Li-Zhu Wu, Li-Ping Zhang, Chen-Ho Tung

Affiliation

¹ Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100101, China.

PMID: 12659577
DOI: 10.1021/ol0341041

Abstract

[reaction: see text] 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(+)(CH(3))(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-tail (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.