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Ring lithiation of 1,8-bis(dimethylamino)naphthalene:another side of the 'proton sponge coin'.
Autorzy
Rok wydania
2015
Czasopismo
Numer woluminu
44
Strony
17756-17766
DOI
10.1039/C5DT02482J
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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.
Adres publiczny
http://dx.doi.org/10.1039/C5DT02482J
Strona internetowa wydawcy
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