Ring lithiation of 1,8-bis(dimethylamino)naphthalene: Another side of the 'proton sponge coin'
Alexander Filarowski
2, 3
,
Peter M. Tolstoy
5
,
Publication type: Journal Article
Publication date: 2015-09-09
scimago Q2
wos Q1
SJR: 0.653
CiteScore: 6.0
Impact factor: 3.3
ISSN: 14779226, 14779234
PubMed ID:
26399216
Inorganic Chemistry
Abstract
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.
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13
Total citations:
13
Citations from 2024:
2
(15.38%)
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GOST
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Antonov A. S. et al. Ring lithiation of 1,8-bis(dimethylamino)naphthalene: Another side of the 'proton sponge coin' // Dalton Transactions. 2015. Vol. 44. No. 40. pp. 17756-17766.
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Antonov A. S., Pozharskii A. F., Ozeryanskii V. A., Filarowski A., Suponitsky K. Y., Tolstoy P. M., Vovk M. A. Ring lithiation of 1,8-bis(dimethylamino)naphthalene: Another side of the 'proton sponge coin' // Dalton Transactions. 2015. Vol. 44. No. 40. pp. 17756-17766.
Cite this
RIS
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TY - JOUR
DO - 10.1039/c5dt02482j
UR - https://xlink.rsc.org/?DOI=C5DT02482J
TI - Ring lithiation of 1,8-bis(dimethylamino)naphthalene: Another side of the 'proton sponge coin'
T2 - Dalton Transactions
AU - Antonov, Alexander S.
AU - Pozharskii, Alexander F.
AU - Ozeryanskii, Valery A.
AU - Filarowski, Alexander
AU - Suponitsky, Kyrill Yu.
AU - Tolstoy, Peter M.
AU - Vovk, Mikhail A
PY - 2015
DA - 2015/09/09
PB - Royal Society of Chemistry (RSC)
SP - 17756-17766
IS - 40
VL - 44
PMID - 26399216
SN - 1477-9226
SN - 1477-9234
ER -
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BibTex (up to 50 authors)
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@article{2015_Antonov,
author = {Alexander S. Antonov and Alexander F. Pozharskii and Valery A. Ozeryanskii and Alexander Filarowski and Kyrill Yu. Suponitsky and Peter M. Tolstoy and Mikhail A Vovk},
title = {Ring lithiation of 1,8-bis(dimethylamino)naphthalene: Another side of the 'proton sponge coin'},
journal = {Dalton Transactions},
year = {2015},
volume = {44},
publisher = {Royal Society of Chemistry (RSC)},
month = {sep},
url = {https://xlink.rsc.org/?DOI=C5DT02482J},
number = {40},
pages = {17756--17766},
doi = {10.1039/c5dt02482j}
}
Cite this
MLA
Copy
Antonov, Alexander S., et al. “Ring lithiation of 1,8-bis(dimethylamino)naphthalene: Another side of the 'proton sponge coin'.” Dalton Transactions, vol. 44, no. 40, Sep. 2015, pp. 17756-17766. https://xlink.rsc.org/?DOI=C5DT02482J.