Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine in the Presence of Chlorotrimethylsilane

Autor:	Hiromu Kawakubo, Hideo Tanaka, Kazuma Kobayashi, Tomotake Yano, Syogo Kamenoue, Manabu Kuroboshi, Tomomi Akagi
Rok vydání:	2011
Předmět:	Reaction mechanism Galvanic anode Organic Chemistry Inorganic chemistry Electrochemistry Catalysis chemistry.chemical_compound Electron transfer chemistry Polymer chemistry Triphenylphosphine Acetonitrile Triphenylphosphine oxide Phosphine
Zdroj:	Synthesis. 2011:4091-4098
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0031-1289612
Popis:	Electroreduction of triphenylphosphine oxide to triphenylphosphine in an acetonitrile solution of tetrabutylammonium bromide in the presence of chlorotrimethylsilane was performed successfully in an undivided cell fitted with a zinc anode and a platinum cathode under constant current. A plausible mechanism involving, (1) one-electron reduction of triphenylphosphine oxide generating the corresponding anion radical [Ph 3 P˙-O - ], (2) subsequent reaction with chlorotrimethylsilane affording the (trimethylsiloxy)triphenylphosphorus radical [Ph 3 P˙-OSiMe 3 ], and (3) further one-electron reduction followed by P-O bond fission leading to triphenylphosphine is proposed. In a similar manner, electroreduction of some triarylphosphine oxides and alkyldiarylphosphine oxides was executed to give the corresponding phosphine derivatives in good to moderate yields.
Databáze:	OpenAIRE
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