The Role of Conjugation in the Halogen‐Lithium Exchange Selectivity: lithiation of 4, 6, 7, 9‐tetrabromo‐1, 3‐dimethyl‐2, 3‐dihydro‐1H‐perimidine

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The Role of Conjugation in the Halogen‐Lithium Exchange Selectivity: lithiation of 4, 6, 7, 9‐tetrabromo‐1, 3‐dimethyl‐2, 3‐dihydro‐1H‐perimidine. / Якубенко, Артем Алексеевич ; Тупикина, Елена Юрьевна ; Антонов, Александр Сергеевич.

In: Chemistry - A European Journal, Vol. 29, No. 46, e202301439, 15.08.2023.

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

BibTeX

@article{43cb1b115921481ba94f740d06a30374,

title = "The Role of Conjugation in the Halogen‐Lithium Exchange Selectivity: lithiation of 4, 6, 7, 9‐tetrabromo‐1, 3‐dimethyl‐2, 3‐dihydro‐1H‐perimidine",

abstract = "The first case of successful suppression of the coordination of a lithium atom with a dialkylamino group by the effective conjugation of the latter with the aromatic core has been discovered. This effect controls regioselectivity of the bromine−lithium exchange in 4,6,7,9-tetrabromo-1,3-dimethyl-2,3-dihydro-1H-perimidine, which leads to products with the most effective conjugation. As a result, the product of this quadruple exchange demonstrates no tendency of the coordination of the NMe groups to neighboring lithium atoms despite the absence of steric restrictions. Experimental results are explained by means of quantum chemical calculations: geometry optimization, natural bond analysis and scans using the modredundant scheme.",

keywords = "conjugation, coordination, naphthalene, organolithiums, regioselectivity",

author = "Якубенко, {Артем Алексеевич} and Тупикина, {Елена Юрьевна} and Антонов, {Александр Сергеевич}",

year = "2023",

month = aug,

day = "15",

doi = "10.1002/chem.202301439",

language = "English",

volume = "29",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-Blackwell",

number = "46",

}

RIS

TY - JOUR

T1 - The Role of Conjugation in the Halogen‐Lithium Exchange Selectivity: lithiation of 4, 6, 7, 9‐tetrabromo‐1, 3‐dimethyl‐2, 3‐dihydro‐1H‐perimidine

AU - Якубенко, Артем Алексеевич

AU - Тупикина, Елена Юрьевна

AU - Антонов, Александр Сергеевич

PY - 2023/8/15

Y1 - 2023/8/15

N2 - The first case of successful suppression of the coordination of a lithium atom with a dialkylamino group by the effective conjugation of the latter with the aromatic core has been discovered. This effect controls regioselectivity of the bromine−lithium exchange in 4,6,7,9-tetrabromo-1,3-dimethyl-2,3-dihydro-1H-perimidine, which leads to products with the most effective conjugation. As a result, the product of this quadruple exchange demonstrates no tendency of the coordination of the NMe groups to neighboring lithium atoms despite the absence of steric restrictions. Experimental results are explained by means of quantum chemical calculations: geometry optimization, natural bond analysis and scans using the modredundant scheme.

AB - The first case of successful suppression of the coordination of a lithium atom with a dialkylamino group by the effective conjugation of the latter with the aromatic core has been discovered. This effect controls regioselectivity of the bromine−lithium exchange in 4,6,7,9-tetrabromo-1,3-dimethyl-2,3-dihydro-1H-perimidine, which leads to products with the most effective conjugation. As a result, the product of this quadruple exchange demonstrates no tendency of the coordination of the NMe groups to neighboring lithium atoms despite the absence of steric restrictions. Experimental results are explained by means of quantum chemical calculations: geometry optimization, natural bond analysis and scans using the modredundant scheme.

KW - conjugation

KW - coordination

KW - naphthalene

KW - organolithiums

KW - regioselectivity

UR - https://www.mendeley.com/catalogue/2519fd12-6da5-371d-ac1f-53c5b933d38b/

U2 - 10.1002/chem.202301439

DO - 10.1002/chem.202301439

M3 - Article

VL - 29

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 46

M1 - e202301439

ER -

ID: 113799928