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- W3044338729 abstract "Organophosphorus zwitterions are one of the most important but elusive intermediates for carbon-carbon bond formation in synthetic chemistry and biology. However, a lack of isolated examples due to their lability has hampered in-depth understanding of structures and their reaction mechanisms. In this study, we crystallographically reveal the solid-state structure of a phosha-Michael adduct engaged in a cage-opened C60 skeleton, which is formed as a kinetic product. This compound exhibits dark brown colour in solution with an intense absorption band that extends to 1000 nm, reflecting intramolecular charge transfer transitions. From the 1,2-dicarbonyl moiety on the conjugated orifice, β-oxo-phosphorus ylide is formed as a thermodynamic product. The reaction mechanism that has long been disputed is examined by experimental and theoretical studies, showing a pathway which includes an SN2 reaction as a key step instead of the hitherto considered carbene pathway." @default.
- W3044338729 created "2020-07-29" @default.
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- W3044338729 date "2020-07-21" @default.
- W3044338729 modified "2023-10-18" @default.
- W3044338729 title "Organophosphorus zwitterions engaged in a conjugated macrocycle on fullerene" @default.
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- W3044338729 doi "https://doi.org/10.1038/s42004-020-00340-x" @default.
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