Acid-Induced Intramolecular Transformations in Mixed Phosphonium-Iodonium Ylides with a Dibenzothiaphosphonium Core.

Authors

Anton S Nenashev, Mikhail V Zavaruev, Sergey A Pisarev, Vitaly A Roznyatovsky, Yury V Timchenko, Igor A Rodin, Andrey V Mironov, Anna S Pavlova, Irina I Levina, Tatiana D Nekipelova, Tatyana A Podrugina

Published in

The Journal of organic chemistry. Nov 13, 2026. Epub Nov 13, 2026.

Abstract

Mixed phosphonium-iodonium ylides with a cyclic dibenzothiaphosphonium fragment undergo acid-induced intramolecular rearrangement with loss of iodobenzene and incorporation of water, affording sulfonium salts in up to 93% yield. This reactivity contrasts with the ring expansion observed for oxygen-bridged analogues. Control experiments support an intramolecular pathway. The initially formed sulfonium diastereomer slowly equilibrates to the more stable diastereomer by S-inversion and ring inversion. Kinetic NMR at different temperatures together with DFT calculations identify S-inversion as the rate-limiting step of isomerization.

PMID:
43020674
Bibliographic data and abstract were imported from PubMed on 13 Nov 2026.

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