Novel electrochemical deoxygenation reaction using diphenylphosphinates

Organic Letters

Volumn 13, Issue 3, 2011, Pages 406-409

  Lam, Kevin ^a   Markó, István E ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

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Indexed keywords

EID: 79851492678     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102714s     Document Type: Article

References (25)

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23. When the electrolysis was carried out at a constant potential of-2.4 V vs Ag/AgCl, only traces of deoxygenated product were isolated.
24. 4 and with 100 mL of DMF, freshly distilled under argon, 600 mg (1.7 mmol) of 1-adamantyldiphenylphosphinate, dissolved in a little DMF, were added to the cathodic compartment and the solution was stirred at 60 °C. Then, the intensity of the current was fixed at 600 mA by using a potentiostat in galvanostatic mode, and the mixture was electrolyzed until completion of the reaction, as shown by TLC or by GC. The cell was then cooled down to room temperature, and the catholyte was carefully diluted with 100 mL of 4 N HCl. The resulting solution was extracted 4 times with 30 mL of ether. The organic phases were pooled and dried over sodium sulphate, and the solvent was removed under reduced pressure. Finally, the crude product was purified by chromatography on silica gel, using pentane as eluent, affording the title compound as a white powder in 92% yield. This material proved to be identical to an authentic sample of adamantane.
25. The corresponding toluate led to the silylated cyclized product.