Ring lithiation of 1,8-bis(dimethylamino)naphthalene: another side of the 'proton sponge coin'

被引：14
|
作者：
Antonov, Alexander S. [1 ]
Pozharskii, Alexander F. [1 ]
Ozeryanskii, Valery A. [1 ]
Filarowski, Aleksander [2 ,3 ]
Suponitsky, Kyrill Yu. [4 ]
Tolstoy, Peter M. [5 ]
Vovk, Mikhail A. [5 ]
机构：
[1] Southern Fed Univ, Dept Organ Chem, Rostov Na Donu 344090, Russia
[2] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
[3] Joint Inst Nucl Res, Frank Lab Neutron Phys, Dubna 141980, Russia
[4] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
[5] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia
来源：
DALTON TRANSACTIONS | 2015年 / 44卷 / 40期
基金：
俄罗斯基础研究基金会;
关键词：
PERI-NAPHTHYLENEDIAMINES; HYDROGEN-BOND; SPECTROSCOPY; CONFORMERS; BASE;
D O I：
10.1039/c5dt02482j
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
It has been found that 1,8- bis(dimethylamino) naphthalene (DMAN), unlike N,N-dimethylaniline, undergoes ring metallation in the n-BuLi-TMEDA-Et2O system with a low selectivity and in poor total yields. The situation is significantly improved in the t-BuLi- TMEDA-n-hexane system when 3- and 4-lithium derivatives become the only reaction products obtained in good yields. The formation of 3-Li-DMAN is especially desired since no method of direct meta-functionalization of DMAN is known to date. The relative stability and structure of DMAN lithium derivatives have been examined with the help of X-ray and multinuclear NMR measurements as well as DFT calculations.
引用
收藏
页码：17756 / 17766
页数：11
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