Phosphonium salts and P-ylides

Selva, Maurizio; Perosa, Alvise; Noè, Marco

doi:10.1039/9781788010689-00139

Cited by 3 publications

(2 citation statements)

References 25 publications

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“…They are already known not only for their use in the Wittig reaction as ylide precursors [1][2][3], but also as convenient building blocks used in many other reactions, especially various types of couplings [4][5][6][7][8]. Moreover, they are successfully used as solvents and catalysts (PILs-phosphonium ionic liquids are good examples here) [9][10][11][12][13]. Due to some specific properties, the presence of a phosphonium group can also influence the biological properties of the whole molecule (e.g., (TPP + )-based mitochondria-targeted compounds) [14].…”

Section: Introductionmentioning

confidence: 99%

1-Hydroxyalkylphosphonium Salts—Synthesis and Properties

Adamek,

Kuźnik,

Październiok-Holewa

et al. 2023

Molecules

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An efficient and convenient method for the synthesis of 1-hydroxyalkylphosphonium salts is described. Reactions were carried out at room temperature, in a short time, and without chromatography for product isolation. The properties of the obtained phosphonium salts were examined and discussed. In this paper, primary attention was paid to the stability of phosphonium salts, depending on the structure of the aldehydes used as substrates in their preparation. Other conditions such as the type of solvent, temperature, and molar ratio of the substrates were also investigated. Finally, the high reactivity of 1-hydroxyalkylphosphonium salts was demonstrated in reactions with amide-type substrates and (hetero)aromatic compounds. The developed step-by-step procedure (with the isolation of 1-hydroxyphosphonium salts) was compared to the one-pot protocol (in situ formation of such phosphonium salts).

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Section: Introductionmentioning

confidence: 99%

1-Hydroxyalkylphosphonium Salts—Synthesis and Properties

Adamek,

Kuźnik,

Październiok-Holewa

et al. 2023

Molecules

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“…This investigation is not only significant for synthesizing new electron-deficient cycloheptatrienes but also for exploring nucleophilic substitution reactions in antiaromatic species, a topic unexplored in the literature. Moreover, the introduction of phosphonium and ammonium heteroatoms traditionally serves to stabilize either a nucleophilic center at the αposition 13,14 or an electrophilic center at the β-position. 11,15−17 In this article we observe α-electrophilic reactivity in zwitterions featuring pyridinium or phosphonium groups attached to the middle atom of an allyl-anion moiety (Scheme 1).…”

mentioning

confidence: 99%

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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