Abstract:
A novel mixed phosphonium–iodonium ylide was synthesized by alkylation of 5-phenyl-5H-dibenzophosphole with phenacyl bromide followed by deprotonation and oxidation of the resulting phosphonium ylide with (diacetoxyiodo)- benzene. The influence of the cyclic nature of the phosphonium moiety on the dynamic E/Z isomerism in the mixed ylide is discussed.
Citation:
A. S. Nenashev, D. A. Dospekhov, T. A. Podrugina, “A new P-heterocyclic type of phosphonium–iodonium ylides based on dibenzophosphole”, Mendeleev Commun., 31:5 (2021), 618–619
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https://www.mathnet.ru/eng/mendc1001
https://www.mathnet.ru/eng/mendc/v31/i5/p618
This publication is cited in the following 6 articles:
G. Fiorani, M. Selva, A. Perosa, Organophosphorus Chemistry, 2024, 58
I. D. Potapov, M. V. Motyakin, T. D. Nekipelova, T. A. Podrugina, “Radical intermediates in the photolysis of the mixed benzoyl-substituted phosphonium-iodonium ylide in different solvents”, Russ Chem Bull, 73:3 (2024), 523
Anton S. Nenashev, Dmitrii A. Dospekhov, Mikhail V. Zavaruev, Irina I. Levina, Vitaly A. Roznyatovsky, Andrey V. Mironov, Anna S. Pavlova, Tatyana A. Podrugina, “Phenoxaphosphonium Mixed Ylides in Ring Expansion Reaction”, J. Org. Chem., 89:9 (2024), 6533
Anton Nenashev, Dmitrii Dospekhov, Mikhail Zavaruev, Ilia Potapov, Irina Levina, Vitaly Roznyatovsky, Andrey Mironov, Sergey Pisarev, Anna Pavlova, Tatyana Podrugina, “Cyclic‐Phenoxaphosphinine‐Based Mixed Phosphonium‐Iodonium Ylides with Electron‐Withdrawing Substituents – Synthesis and Structural Features”, ChemistrySelect, 8:37 (2023)
Nicolas D'Imperio, Valentina Pelliccioli, Sara Grecchi, Alberto Bossi, Francesca Vasile, Silvia Cauteruccio, Anna I. Arkhypchuk, Arvind Kumar Gupta, Andreas Orthaber, Sascha Ott, Emanuela Licandro, “Highly Conjugated Bis(benzo[b]phosphole)‐P‐oxides: Synthesis and Electrochemical, Optical, and Computational Studies”, Eur J Org Chem, 26:4 (2023)
I. D. Potapov, A. Yu. Voznarskiy, A. V. Mironov, M. V. Motyakin, T. D. Nekipelova, T. A. Podrugina, “Regioselective heterocyclization of mixed phosphonium-iodonium ylides with acetylenes involving dimethyl acetylenedicarboxylate”, Russ Chem Bull, 71:5 (2022), 1027
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