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Alcoholysis Versus Fission of the Ester Group During the Reaction of Dialkyl Phenylphosphonates in the Presence of Ionic Liquids

[ Vol. 25 , Issue. 7 ]

Author(s):

Nikoletta Harsági, Csilla Bertha, Nóra Zsuzsa Kiss, Réka Henyecz, Petra Regina Varga, Péter Ábrányi-Balogh, László Drahos and György Keglevich*   Pages 842 - 848 ( 7 )

Abstract:


In the microwave-assisted alcoholysis of dialkyl phenylphosphonates performed in the presence of suitable ionic liquids, such as [bmim][BF4] or [bmim][PF6], affording the phosphonate with mixed alkoxy groups and the fully transesterified product, the fission of the phosphonate function to the ester-acid or diacid moiety was inevitable. Moreover, in the presence of [emim][HSO4], the reaction could be performed to afford the phosphonic esteracid with a selectivity of 66% and the diacid with a selectivity of 97%. The ester-acids provided by the new protocol may be valuable intermediates.

Keywords:

Dialkyl phosphonates, microwave, alcoholysis, ionic liquid, phosphonic ester-acid, phosphonic acid

Affiliation:

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Research Centre for Natural Sciences, Medicinal Chemistry Research Group, 1117 Budapest, Research Centre for Natural Sciences, MS Proteomics Research Group, 1117 Budapest, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest

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