Reaction of sodium bis(trimethylsilyl)amide with bromotoluenes

被引：0
作者：
A. V. Lis
I. P. Tsyrendorzhieva
A. I. Albanov
B. A. Shainyan
V. I. Rakhlin
机构：
[1] Russian Academy of Sciences,Favorskii Irkutsk Institute of Chemistry, Siberian Branch
来源：
Russian Journal of Organic Chemistry | 2015年 / 51卷
关键词：
Aniline; Trimethylsilyl; Bromobenzene; Rearrangement Product; Silyl Group;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Isomeric bromotoluenes react with sodium bis(trimethylsilyl)amide through intermediate methylbenzynes, yielding N,N-bis(trimethylsilyl)toluidines and rearrangement products, N,2-bis(trimethylsilyl)toluidines. The formation of the latter is a rare example of 1,3-migration of silyl group from nitrogen atom to aromatic carbon atom. The rearrangement is favored by increased solvent polarity and elevated temperature. The observed product ratio can be rationalized by DFT quantum chemical calculations.
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页码：335 / 340
页数：5
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