PHOTOCHEMISTRY OF SUBSTITUTED BENZOYLFORMATE ESTERS - A CONVENIENT METHOD FOR THE PHOTOCHEMICAL OXIDATION OF ALCOHOLS

被引：27

作者：

PIRRUNG, MC

TEPPER, RJ

机构：

[1] Department of Chemistry, P. M. Gross Chemical Laboratory, Duke University, Durham

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 08期

关键词：

D O I：

10.1021/jo00113a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The production of aldehydes and ketones via photochemical hydrogen atom transfer in substituted benzoylformate esters of primary and secondary alcohols has been investigated. Substituent effect studies have shown that (2,4-dimethoxybenzoyl)formate (DMBF) esters give superior performance. A divergence in the byproducts derived from the ester group (the benzaldehyde (and presumably CO) or the benzoic acid (and presumably CO2)) is observed depending on the presence of oxygen. A mechanistic rationale for the formation of the benzoic acid has been advanced based on the known trapping of intermediate 1,4-biradicals by oxygen followed by fragmentation.

引用

页码：2461 / 2465

页数：5

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