In situ alcohol oxidation-Wittig reactions

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3815-3818

  Wei, Xudong ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; BENZYL ALCOHOL; COLABOMYCIN A; MANGANESE DIOXIDE;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL REACTION; EXTRACTION; ISOMERISM; MOLECULAR STABILITY; SYNTHESIS;

EID: 0032575183     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00592-9     Document Type: Article

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12. 13C NMR spectroscopy and by elemental analysis or high resolution mass spectrometry.
13. 9. Representative procedure: At RT, manganese dioxide (Aldrich, activated, 0.87 g, 10 mmol) was added in 5 portions over 5 h to a stirred solution of 2,3-dibromobuten-1,4-diol (24) (123 mg, 0.5 mmol) and (carboethoxymethylene)triphenylphosphorane (418 mg, 1.2 mmol) in dichloromethane (25 ml). The resulting reaction mixture was stirred for ca. 15 h until t.l.c. indicated that the reaction was complete. The manganese dioxide was removed by filtration, washed well with dichloromethane, and the combined organic portions were concentrated to ca. 1-2 ml. Column chromatography (PE-ether, 7:1) gave E,E,E-triene (25) (160 mg, 84%) as a white crystalline solid, m.p. 145-147°C, which was fully characterised.
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