Current Green Chemistry

György Keglevich
Budapest University of Technology and Economics
Budapest
Hungary

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Silanes as Reagents for the Deoxygenation of Tertiary Phosphine Oxides – A Case Study for the Deoxygenation of 5-Membered Cyclic Phosphine Oxides

Author(s): Gyorgy Keglevich and Tamara Kovacs

Affiliation: Department of Organic Chemical Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.

Keywords: Cyclic phosphine/phosphane oxides, phospholene oxides, deoxygenation, silanes, phosphines/phosphanes, phosphine/phosphane sulfides, phosphine boranes, user friendly reagents.

Abstract:

The possibilities for the deoxygenation of 3-methyl-1-phenyl-3-phospholene 1-oxide were investigated using different silanes. Cl3SiH and PhSiH3 were efficient, but they have disadvantages regarding user-friendliness and price, respectively. Tetramethyldisiloxane and polymethylhydrosiloxane that are cheap and user-friendly, but are of lower reactivity could be applied at 110 °C in toluene solution, without the use of any catalyst successfully. Then, the deoxygenation was extended to other 1-phenylphospholene oxides and phospholane oxides. The cyclic phosphines useful as ligands in transition metal complexes were identified as their sulfides and boranes. The catalyst-free method elaborated seems to be of more general value.

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Article Details

VOLUME: 1
ISSUE: 2
Page: [182 - 188]
Pages: 7
DOI: 10.2174/2213346101666140115214100