An unusual route to deoxysugars by hydrogen atom transfer from cyclohexane. Possible manifestation of polar effects in a radical process

Journal of the American Chemical Society

Volumn 118, Issue 38, 1996, Pages 9190-9191

  Quiclet Sire, Béatrice ^a   Zard, Samir Z ^a,b  

^a CNRS   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYSUGAR;

ARTICLE; CARBOHYDRATE SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029828028     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9619622     Document Type: Article

References (40)

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40. Typical experimental procedure: A solution of the xanthate (1 mmol) in degassed cyclohexane (7 mL) or a 9:1 mixture of cyclohexane and 1,2-dichloroethane was heated under reflux and lauroyl peroxide was added portionwise (2% every 2 h) until the starting material was consumed (6-15% was needed depending on the substrate). The solvents were evaporated under reduced pressure, and the residue purified by chromatography on a silica gel column to afford the deoxygenated derivative.