Preparation of olefins from alcohols by thermal rearrangement of propargylic xanthates

Tetrahedron Letters

Volumn 40, Issue 7, 1999, Pages 1305-1308

  Fauré Tromeur, Mélanie ^a   Zard, Samir Z ^a,b  

^a CNRS   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE; XANTHIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; DEHYDRATION; DRUG SYNTHESIS; PYROLYSIS; REACTION ANALYSIS; THERMOREGULATION; THIN LAYER CHROMATOGRAPHY;

EID: 0033547942     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02669-0     Document Type: Article

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33. Typical experimental procedure: A solution of xanthate 1g (0.5 mmol.) and salt 2 (0.05 mmol.) in toluene (5 ml) was heated to reflux for several hours. The solution was allowed to cool and the crude product was purified by chromatography after removal of the solvent to give 2-cholestene 3g in 88% yield. Xanthates 1a, 1b, le, 1d, 1e, 1f, 1g, 1h and 1i were obtained by alkylation with propargyl bromide of the xanthate salts derived from the respective alcohols and carbon disulfide.
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