Phosphonium salts and P-ylides

Fiorani, G.; Selva, M.; Perosa, A.

doi:10.1039/9781839166198-00125

Organophosphorus Chemistry

2022

DOI: 10.1039/9781839166198-00125

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Phosphonium salts and P-ylides

G. Fiorani¹,

M. Selva²,

A. Perosa³

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2024

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

Sokolova,

Platonov,

Belyy

et al. 2024

Org. Lett.

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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 Mobius aromaticity, as evidenced by nuclear independent chemical shift values and the shape of its HOMO. This study represents the eighth confirmed instance of a Mobius-aromatic organic species in its ground state.

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

Sokolova,

Platonov,

Belyy

et al. 2024

Org. Lett.

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show abstract

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Phosphonium salts and P-ylides

Cited by 1 publication

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

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

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Phosphonium salts and P-ylides

Cited by 1 publication

References 0 publications

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

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

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