BENZIMIDAZOLINE-DIMETHOXYPYRENE. AN EFFECTIVE PROMOTER SYSTEM FOR PHOTOINDUCED ELECTRON TRANSFER PROMOTED REDUCTIVE TRANSFORMATIONS OF ORGANIC COMPOUNDS

被引：28

作者：

Hasegawa, Eietsu ^{[1
]}

Hirose, Harumi ^{[1
]}

Sasaki, Kosuke ^{[1
]}

Takizawa, Shinya ^{[1
]}

Seida, Takayuki ^{[1
]}

Chiba, Naoki ^{[1
]}

机构：

[1] Niigata Univ, Dept Chem, Fac Sci, Niigata 9502181, Japan

来源：

HETEROCYCLES | 2009年 / 77卷 / 02期

关键词：

Benzimidazoline; Dimethoxypyrene; Photoinduced Electron Transfer; Radical Ion; Reductive Transformation; ALPHA; BETA-EPOXY KETONES; HYDROGEN-ATOM; CARBONYL-COMPOUNDS; HYDRIDE TRANSFER; ION-PAIRS; 1,3-DIMETHYL-2-PHENYLBENZIMIDAZOLINE; CYCLIZATION; OXIDATION; ACID;

D O I：

10.3987/COM-08-S(F)94

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(p-Methoxyphenyl)-1,3-dimethylbenzimidazoline (ADMBI) and 2-(o-hydroxyphenyl)-1,3-dimethylbenzimidazoline (HPDMBI) are used as reducing reagents in 1,8-dimethoxypyrene (1,8-DMP) sensitized, photoinduced electron transfer (PET) reactions. This system was effectively used for PET induced, reductive transformations of various organic substrates, including alpha,beta-epoxy ketones, the olefin tethered 2-bromomethyl-1-tetraone, and o-allyloxy-iodobenzene, as well as for the deprotection reactions of dodecyl-2-benzoylbenzoate and N-sulfonylindole. The results of studies show that 1,8-DMP is a more effective sensitizer than the previously used 9-methylcarbazole for deprotection of N-methyl-4-picolinium ester.

引用

页码：1147 / 1161

页数：15

共 58 条

[1]

[Anonymous], 1993, FUNDAMENTAL PHOTOIND

[2]

Balzani V., 2001, ELECT TRANSFER CHEM, V1-5

[3] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].