Tervalent phosphorus acid derivatives

Hewson, Alan T.

doi:10.1039/b603845j

Cited by 2 publications

(1 citation statement)

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“…Trivalent organophosphorus compounds, that is, phosphites expressed as a chemical formula of P(OR) 3 , have been extensively investigated as reducing agents, [1] metal‐free catalysts, [2] transition‐metal ligands, [3] and π‐conjugated functionalized materials [4] . Importantly, phosphoryl functionalization has been a powerful tool for the C−C bond formation, as well as umpolung of carbonyl groups, both of which are thus frequently employed in syntheses of numerous industrial and natural products [5]…”

Section: Figurementioning

confidence: 99%

Nonclassical Abramov Products Formed on Orifices of Cage‐Opened C₆₀Derivatives

Hashikawa

Okamoto

Murata

2021

Chemistry A European J

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By nucleophilic addition of phosphite P(OMe)3 to a cage‐opened C60 derivative, α‐hydrophosphate and enol phosphate were obtained as kinetic and thermodynamic products, respectively. Different from classical Abramov products bearing a phosphorus–carbon bond, these products have a phosphorus–oxygen bond. The observed anomaly originates from the fully conjugated π system, which significantly stabilizes zwitterionic intermediates bearing a phosphorus–oxygen bond. The thus formed enol phosphate was found to exhibit an intense absorption band that extended to 730 nm, reflecting the intramolecular charge‐transfer transitions. We also report domino phosphorylation reactions, which gave a cage‐opened C60 derivative bearing a direct P−C bond.

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Section: Figurementioning

confidence: 99%