Synthesis of uracil derivatives by oxidation of Fischer tungsten-carbene uracil complexes

Journal of Organometallic Chemistry

Volumn 692, Issue 8, 2007, Pages 1623-1627

  Sala, Giorgio Della ^a   Artillo, Antonietta ^a   Ricart, Susagna ^b   Spinella, Aldo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

Fischer carbene complexes; Oxidation; t Butyl hydroperoxide; Uracils

Indexed keywords

CHEMICAL MODIFICATION; COMPLEXATION; NITROGEN; ORGANOMETALLICS; OXIDATION; SUBSTITUTION REACTIONS;

CARBENE; FISCHER CARBENE COMPLEXES; OXIDANTS; T-BUTYL HYDROPEROXIDE; URACIL COMPLEXES;

TUNGSTEN COMPOUNDS;

EID: 33847039205     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.12.013     Document Type: Article

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38. Typical procedure of oxidation of carbene complexes 2 with TBHP: In a screw capped ACE tube containing a solution of metallocarbene 2 (0.1 mmol) in 1,2-dichloroethane, a solution of TBHP (5.5 M in n-decane, 1 mmol) was added. The mixture was warmed at 70 °C until completion of oxidation. Decoloration of solution and formation of a white precipitate was indicative of transformation. Sodium sulfite (10%) aqueous solution (6 ml) was added and the resulting mixture was stirred for 3 h then extracted with dichloromethane. The organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography using chloroform-methanol mixtures as eluant afforded uracil 3.