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Lithiation of 2,4,5,7-Tetrabromo-1,8-bis(dimethylamino)naphthalene: Peculiarities of Directing Groups’ Effects and the Possibility of Polymetalation. / Якубенко, Артем Алексеевич; Карпов, Валерий Владимирович; Тупикина, Елена Юрьевна; Антонов, Александр Сергеевич.

In: Organometallics, Vol. 40, No. 21, 08.11.2021, p. 3627-3636.

Research output: Contribution to journal › Article › peer-review

Harvard

Якубенко, АА, Карпов, ВВ, Тупикина, ЕЮ & Антонов, АС 2021, 'Lithiation of 2,4,5,7-Tetrabromo-1,8-bis(dimethylamino)naphthalene: Peculiarities of Directing Groups’ Effects and the Possibility of Polymetalation', Organometallics, vol. 40, no. 21, pp. 3627-3636. https://doi.org/10.1021/acs.organomet.1c00489

APA

Якубенко, А. А., Карпов, В. В., Тупикина, Е. Ю., & Антонов, А. С. (2021). Lithiation of 2,4,5,7-Tetrabromo-1,8-bis(dimethylamino)naphthalene: Peculiarities of Directing Groups’ Effects and the Possibility of Polymetalation. Organometallics, 40(21), 3627-3636. https://doi.org/10.1021/acs.organomet.1c00489

Vancouver

Якубенко АА, Карпов ВВ, Тупикина ЕЮ, Антонов АС. Lithiation of 2,4,5,7-Tetrabromo-1,8-bis(dimethylamino)naphthalene: Peculiarities of Directing Groups’ Effects and the Possibility of Polymetalation. Organometallics. 2021 Nov 8;40(21):3627-3636. https://doi.org/10.1021/acs.organomet.1c00489

Author

Якубенко, Артем Алексеевич ; Карпов, Валерий Владимирович ; Тупикина, Елена Юрьевна ; Антонов, Александр Сергеевич. / Lithiation of 2,4,5,7-Tetrabromo-1,8-bis(dimethylamino)naphthalene: Peculiarities of Directing Groups’ Effects and the Possibility of Polymetalation. In: Organometallics. 2021 ; Vol. 40, No. 21. pp. 3627-3636.

BibTeX

@article{b7ccbbfbbce44a7fac2a46d952ce6c6d,
title = "Lithiation of 2,4,5,7-Tetrabromo-1,8-bis(dimethylamino)naphthalene: Peculiarities of Directing Groups{\textquoteright} Effects and the Possibility of Polymetalation",
abstract = "The bromine-lithium exchange sequence upon interaction of 2,4,5,7-tetrabromo-1,8-bis(dimethylamino)naphthalene with n-BuLi was studied. Experimental results were explained by means of quantum chemical calculations. It was demonstrated that the first exchange occurs in position 4 due to the significant decrease of a steric strain of the molecule. The second exchange takes place in either position 5 or 7 due to the even more negative charge distribution in the naphthalene core. As a result, the third exchange leads to the species containing lithium in positions 2,4,5 or 2,4,7. Using a large excess of n-BuLi in hexane, 2,4,5,7-tetralithio-1,8-bis(dimethylamino)naphthalene was successfully prepared. The latter was used for the synthesis of several tetrasubstituted derivatives of 1,8-bis(dimethylamino)naphthalene by quenching with different electrophiles.",
keywords = "BOND, ENERGIES, ORGANOLITHIUM COMPOUNDS, PERI-NAPHTHYLENEDIAMINES, SPONGE, WAVE-FUNCTION",
author = "Якубенко, {Артем Алексеевич} and Карпов, {Валерий Владимирович} and Тупикина, {Елена Юрьевна} and Антонов, {Александр Сергеевич}",
note = "Publisher Copyright: {\textcopyright}",
year = "2021",
month = nov,
day = "8",
doi = "10.1021/acs.organomet.1c00489",
language = "English",
volume = "40",
pages = "3627--3636",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "21",

}

RIS

TY - JOUR

T1 - Lithiation of 2,4,5,7-Tetrabromo-1,8-bis(dimethylamino)naphthalene: Peculiarities of Directing Groups’ Effects and the Possibility of Polymetalation

AU - Якубенко, Артем Алексеевич

AU - Карпов, Валерий Владимирович

AU - Тупикина, Елена Юрьевна

AU - Антонов, Александр Сергеевич

N1 - Publisher Copyright: ©

PY - 2021/11/8

Y1 - 2021/11/8

N2 - The bromine-lithium exchange sequence upon interaction of 2,4,5,7-tetrabromo-1,8-bis(dimethylamino)naphthalene with n-BuLi was studied. Experimental results were explained by means of quantum chemical calculations. It was demonstrated that the first exchange occurs in position 4 due to the significant decrease of a steric strain of the molecule. The second exchange takes place in either position 5 or 7 due to the even more negative charge distribution in the naphthalene core. As a result, the third exchange leads to the species containing lithium in positions 2,4,5 or 2,4,7. Using a large excess of n-BuLi in hexane, 2,4,5,7-tetralithio-1,8-bis(dimethylamino)naphthalene was successfully prepared. The latter was used for the synthesis of several tetrasubstituted derivatives of 1,8-bis(dimethylamino)naphthalene by quenching with different electrophiles.

AB - The bromine-lithium exchange sequence upon interaction of 2,4,5,7-tetrabromo-1,8-bis(dimethylamino)naphthalene with n-BuLi was studied. Experimental results were explained by means of quantum chemical calculations. It was demonstrated that the first exchange occurs in position 4 due to the significant decrease of a steric strain of the molecule. The second exchange takes place in either position 5 or 7 due to the even more negative charge distribution in the naphthalene core. As a result, the third exchange leads to the species containing lithium in positions 2,4,5 or 2,4,7. Using a large excess of n-BuLi in hexane, 2,4,5,7-tetralithio-1,8-bis(dimethylamino)naphthalene was successfully prepared. The latter was used for the synthesis of several tetrasubstituted derivatives of 1,8-bis(dimethylamino)naphthalene by quenching with different electrophiles.

KW - BOND

KW - ENERGIES

KW - ORGANOLITHIUM COMPOUNDS

KW - PERI-NAPHTHYLENEDIAMINES

KW - SPONGE

KW - WAVE-FUNCTION

UR - http://www.scopus.com/inward/record.url?scp=85118647119&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/8a2b1e36-3858-3a6b-b16e-783502620bcb/

U2 - 10.1021/acs.organomet.1c00489

DO - 10.1021/acs.organomet.1c00489

M3 - Article

VL - 40

SP - 3627

EP - 3636

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 21

ER -

ID: 87508679