Synthesis of new organophosphorus compounds using the atherton–todd reaction as a versatile tool
Corresponding Author
Sebastian Wagner
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, GermanySearch for more papers by this authorMuriel Rakotomalala
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorYana Bykov
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorOlaf Walter
European Commission Joint Research Centre, Institute for Transuranium Elements, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorManfred Döring
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorCorresponding Author
Sebastian Wagner
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, GermanySearch for more papers by this authorMuriel Rakotomalala
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorYana Bykov
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorOlaf Walter
European Commission Joint Research Centre, Institute for Transuranium Elements, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorManfred Döring
Institute of Catalysis Research and Technology, Karlsruhe Institute of Technology, 76344 Eggenstein-Leopoldshafen, Germany
Search for more papers by this authorAbstract
This article discusses the behavior of seven organophosphorus compounds under Atherton–Todd conditions. Therefore, the reactivity and selectivity of different (phen)oxaphosphinines, dioxaphosphinines, dioxaphosphinanes, and diphenylphosphine oxide with three nucleophiles were systematically studied. The results prove the versatility of the Atherton–Todd reaction to a broad range of organophosphorus compounds with different phosphorus environments and reactive PH bonds. The nucleophiles studied in this article were chosen as model substrates for amines and alcohols. Because organophosphorus molecules are important and versatile compounds, for a broad field of applications, novel synthetic approaches are of interest to both academia and industry. As an example, the single-step synthesis of the bridged 1,3-phenylene bis(diphenylphosphinate) with potential flame-retardant properties was added to this study. In addition, the reaction is utilized for the synthesis of a novel organophosphorus anhydride. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:216–222, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21006
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