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Chemistry of phosphorus ylides. Part 25 [1]. Interaction of hexaphenylcarbodiphosphorane with carbonyls, hydrazone, and Mannich bases. A synthesis of phosphoranylidenes, phosphobetaines, and oxaphosphinin

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Abstract

The reaction of the allylic hexaphenylcarbodiphosphorane with carbonyls afforded the corresponding phosphoranylidene derivatives. On the other hand, the stable phosphorbetaines were obtained when the bisphosphorane was allowed to react with the α-diketone and triketone. The azaphosphoranylidene was isolated from the reaction of the bisphosphorane with hydrazone. Moreover, the bisphosphorane reacted with niclosamide and quinoline Mannich bases with the formation of the oxaphosphinins. When the Wittig reaction was performed with the new phosphoranes, the corresponding exocyclic olefins were obtained. On the other hand, the oxaphosphinins were produced when the phosphoranes were treated under the condition of a Hoffmann degradation reaction.

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Authors and Affiliations

  1. Department of Organometallic and Organometalloide Chemistry, National Research Centre, Dokki, Cairo, Egypt

    Medhat M. Said, Soher S. Maigali, Mansoura A. Abd-El-Maksoud & Fouad M. Soliman

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  1. Medhat M. Said
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  2. Soher S. Maigali
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  3. Mansoura A. Abd-El-Maksoud
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  4. Fouad M. Soliman
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Correspondence to Medhat M. Said.

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Correspondence: Medhat M. Said, Department of Organometallic and Organometalloide Chemistry, National Research Centre, El-Tahrir Street, Dokki, Cairo, Egypt.

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Said, M., Maigali, S., Abd-El-Maksoud, M. et al. Chemistry of phosphorus ylides. Part 25 [1]. Interaction of hexaphenylcarbodiphosphorane with carbonyls, hydrazone, and Mannich bases. A synthesis of phosphoranylidenes, phosphobetaines, and oxaphosphinin. Monatsh Chem 139, 1299–1306 (2008). https://doi.org/10.1007/s00706-007-0843-7

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