The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate DOI

Alena D. Sokolova,

Dmitry N. Platonov,

Alexander Yu. Belyy

и другие.

Organic Letters, Год журнала: 2024, Номер 26(28), С. 5877 - 5882

Опубликована: Июль 3, 2024

Antiaromatic nucleophilic substitution reactions in cycloheptatrienide pyridinium and phosphonium zwitterions with initial formation of a cycloheptatetraene intermediate are explored. The mechanism was supported by quantum chemical calculations, first-order reaction kinetics, high-resolution mass spectrometry. zwitterion exhibited weak antiaromaticity, whereas the displayed Möbius aromaticity, as evidenced nuclear independent shift values shape its HOMO. This study represents eighth confirmed instance Möbius-aromatic organic species ground state.

Язык: Английский

Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones DOI

Alexander Yu. Belyy,

Alena D. Sokolova,

Rinat F. Salikov

и другие.

Mendeleev Communications, Год журнала: 2025, Номер 35(2), С. 162 - 164

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

1
The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate DOI

Alena D. Sokolova,

Dmitry N. Platonov,

Alexander Yu. Belyy

и другие.

Organic Letters, Год журнала: 2024, Номер 26(28), С. 5877 - 5882

Опубликована: Июль 3, 2024

Antiaromatic nucleophilic substitution reactions in cycloheptatrienide pyridinium and phosphonium zwitterions with initial formation of a cycloheptatetraene intermediate are explored. The mechanism was supported by quantum chemical calculations, first-order reaction kinetics, high-resolution mass spectrometry. zwitterion exhibited weak antiaromaticity, whereas the displayed Möbius aromaticity, as evidenced nuclear independent shift values shape its HOMO. This study represents eighth confirmed instance Möbius-aromatic organic species ground state.

Язык: Английский

Процитировано

2