C-O bond fragmentation of 4-picolyl- and N-methyl-4-picolinium esters triggered by photochemical electron transfer

被引：48

作者：

Sundararajan, C ^{[1
]}

Falvey, DE ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 17期

关键词：

D O I：

10.1021/jo049501j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photochemical reduction of several 4-picolyl- and N-methyl-4-picolinium esters was examined using product analysis, laser flash photolysis, and fluorescence quenching. It is demonstrated that the radical (anions) formed in these reactions readily fragment to yield a carboxylic acid and a 4-pyridylmethyl radical intermediate. The high chemical and quantum yields observed for these photoreactions suggests that these esters can be used as photolabile protecting groups.

引用

页码：5547 / 5554

页数：8

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