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

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

Журнал

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Вых. Данные

Год: 2024, Том: 26, Номер: 28, Страницы: 5877-5882 Страниц : 6 DOI: 10.1021/acs.orglett.4c01446

Авторы

Sokolova Alena D. ¹ , Platonov Dmitry N. ¹ , Belyy Alexander Yu. ¹ , Salikov Rinat F. ¹ , Erokhin Kirill S. ¹ , Tomilov Yury V. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

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, and high-resolution mass spectrometry. The pyridinium zwitterion exhibited weak antiaromaticity, whereas the intermediate displayed Möbius aromaticity, as evidenced by nuclear independent chemical shift values and the shape of its HOMO. This study represents the eighth confirmed instance of a Möbius-aromatic organic species in its ground state.

Sokolova A.D. , Platonov D.N. , Belyy A.Y. , Salikov R.F. , Erokhin K.S. , Tomilov Y.V.
The Antiaromatic Nucleophilic Substitution Reaction (SNAAr) in Cycloheptatrienyl-Anion Containing Zwitterions with a Möbius-Aromatic Intermediate
Organic Letters. 2024. V.26. N28. P.5877-5882. DOI: 10.1021/acs.orglett.4c01446 WOS Scopus OpenAlex

≡ Web of science:	WOS:001265711200001
≡ Scopus:	2-s2.0-85197489798
≡ OpenAlex:	W4400281570