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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
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.
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页码:1147 / 1161
页数:15
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