Lactone-derived carbon-centered radicals: Formation and reactivity with oxygen

被引:72
作者
Bejan, EV [1 ]
Font-Sanchis, E [1 ]
Scaiano, JC [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/ol0167917
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Several lactones were examined to test the reactivity of carbon-centered radicals toward oxygen. Notably, the radical derived from 2-coumaranone (4) is unreactive toward oxygen, while 2-cuomaranone itself shows enhanced reactivity toward hydrogen abstraction by alkoxyl radicals. We propose that five parameters influence diminished reactivity toward oxygen, i.e., (a) benzylic resonance stabilization, (b) unpaired spin delocalization on oxygen, (c) favorable stereoelectronic effects, (d) electron-withdrawing effects, and (e) steric effects.
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页码:4059 / 4062
页数:4
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