Phenoxaphosphonium Mixed Ylides in Ring Expansion Reaction

Phenoxaphosphonium Mixed Ylides in Ring Expansion Reaction

Treatment of mixed phosphonium–iodonium ylides featuring a six-membered phenoxaphosphonium fragment with aqueous tetrafluoroboronic acid induces a rearrangement, resulting in expansion of the phosphacycle and oxidation of the phosphorus atom. The target difficult-to-access dibenzo­[b,f]­[1,4]­oxapho...

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Veröffentlicht in:Journal of organic chemistry 2024-05, Vol.89 (9), p.6533-6538
Hauptverfasser: Nenashev, Anton S., Dospekhov, Dmitrii A., Zavaruev, Mikhail V., Levina, Irina I., Roznyatovsky, Vitaly A., Mironov, Andrey V., Pavlova, Anna S., Podrugina, Tatyana A.
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container_end_page 6538
container_issue 9
container_start_page 6533
container_title Journal of organic chemistry
container_volume 89
creator Nenashev, Anton S.
Dospekhov, Dmitrii A.
Zavaruev, Mikhail V.
Levina, Irina I.
Roznyatovsky, Vitaly A.
Mironov, Andrey V.
Pavlova, Anna S.
Podrugina, Tatyana A.
description Treatment of mixed phosphonium–iodonium ylides featuring a six-membered phenoxaphosphonium fragment with aqueous tetrafluoroboronic acid induces a rearrangement, resulting in expansion of the phosphacycle and oxidation of the phosphorus atom. The target difficult-to-access dibenzo­[b,f]­[1,4]­oxaphosphepine oxides (3 examples) were isolated in excellent yields (up to 95%) as mixtures of stereoisomers. Hydrolysis of a five-membered mixed ylide, a dibenzophosphole derivative, predominantly preserves the phosphole system with cycle expansion occurring as a side process.
doi_str_mv 10.1021/acs.joc.4c00047
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title Phenoxaphosphonium Mixed Ylides in Ring Expansion Reaction
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