Debromination of 8-bromo-2′-deoxyguanosine by methylene blue and visible light

被引:5
作者
Venkatarangan, L [1 ]
Yang, DH [1 ]
Epling, GA [1 ]
Basu, AK [1 ]
机构
[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA
关键词
electron transfer; photolysis; dehalogenation; nucleoside;
D O I
10.1016/S0040-4039(99)00005-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Debromination of 8-bromo-2'-deoxyguanosine was accomplished in high yield under neutral conditions in aqueous methanol by irradiating with visible light in the presence of methylene blue as a sensitizer and triethylamine as an electron donor. The method can be extended for the debromination of other bromoaromatic compounds. (C) 1999 Elsevier Science Ltd. Ail rights reserved.
引用
收藏
页码:1441 / 1444
页数:4
相关论文
共 14 条
[1]  
Amatore C., 2016, ORGANIC ELECTROCHEMI
[2]   KINETICS OF DISSOCIATIVE ELECTRON-TRANSFER - DIRECT AND MEDIATED ELECTROCHEMICAL REDUCTIVE CLEAVAGE OF THE CARBON HALOGEN BOND [J].
ANDRIEUX, CP ;
SAVEANT, JM ;
SU, KB .
JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (16) :3815-3823
[3]  
BUNCE NJ, 1982, J ORG CHEM, V47, P1948, DOI 10.1021/jo00349a024
[4]  
Cavallaro CL, 1996, NEW J CHEM, V20, P253
[5]   MECHANISTIC ASPECTS OF THE TRIETHYLAMINE ASSISTED PHOTOINDUCED DEHALOGENATION OF HALOGENO-AROMATIC COMPOUNDS [J].
DAVIDSON, RS ;
GOODIN, JW .
TETRAHEDRON LETTERS, 1981, 22 (02) :163-166
[6]  
ELVING PJ, 1953, RECORD CHEMICAL PROG, V14, P99
[7]   EFFICIENT UTILIZATION OF VISIBLE-LIGHT IN THE PHOTOREDUCTION OF CHLOROAROMATIC COMPOUNDS [J].
EPLING, GA ;
WANG, QX ;
QIU, QW .
CHEMOSPHERE, 1991, 22 (9-10) :959-962
[8]  
GORDEEVA LS, 1984, KHIM PRIR SOEDIN, V6, P771
[9]  
Jaiswal DK, 1996, J LABELLED COMPD RAD, V38, P743
[10]   PHOTOCHEMISTRY OF AROMATIC-COMPOUNDS - MECHANISM OF AMINE-ACCELERATED PHOTODEBROMINATION OF 5-BROMO-2-METHOXYPYRIMIDINE [J].
NASIELSKI, J ;
KIRSCHDE.A .
TETRAHEDRON, 1973, 29 (20) :3153-3157