Chemistry of arylalkyl radical cations: Deprotonation vs nucleophilic attack

被引：17
|
作者：
Tolbert, LM
Li, ZZ
Sirimanne, SR
VanDerveer, DG
机构：
[1] School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 12期
关键词：
D O I：
10.1021/jo961502r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Radical-cation-mediated oxidation of 9-methylanthracene (9MA) by pyridine/iodine in chloroform produces mainly the product of nucleophilic attack at the open C-10 position. When methyl is replaced by ethyl as in 9-ethylanthracene (9EA), the nucleophilic product is the only one observed. Alternatively, aceanthrene (AA), the 1,9-ethano-bridged equivalent of 9EA, produces mainly the product of side-chain substitution. Stereoelectronic control in the deprotonation is proposed as the rationale for this difference in reactivity, as well as for other radical-cation-mediated oxidations.
引用
收藏
页码：3927 / 3930
页数：4
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