title: Ring lithiation of 1,8-bis(dimethylamino)naphthalene: another side of the 'proton sponge coin'.
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.
authors.affiliation: Department of Organic Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation. apozharskii@sfedu.ru.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Antonov
authors.forename: Alexander F
authors.initials: AF
authors.lastname: Pozharskii
authors.forename: Valery A
authors.initials: VA
authors.lastname: Ozeryanskii
authors.forename: Aleksander
authors.initials: A
authors.lastname: Filarowski
authors.forename: Kyrill Yu
authors.initials: KY
authors.lastname: Suponitsky
authors.forename: Peter M
authors.initials: PM
authors.lastname: Tolstoy
authors.forename: Mikhail A
authors.initials: MA
authors.lastname: Vovk