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Synlett 1998; 1998(1): 39-40
DOI: 10.1055/s-1998-1582
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Radical Deoxygenation of Alcohols via Their S-Methyl Dithiocarbonate Derivatives with Di-n-butylphosphine Oxide as Hydrogen Atom Donor

Doo Ok Jang* , Dae Hyan Cho, Derek H. R. Barton
  • *Department of Chemistry, Yonsei University, Wonju 220-710, Korea; Fax 82 3 71 7 63 43 23; E-mail: dojang@dragon.yonsei.ac.kr
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Publication Date:
31 December 2000 (online)

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Various S-methyl dithiocarbonates of tertiary and secondary alcohols are readily deoxygenated in high isolated yields by radical deoxygenation with di-n-butylphosphine oxide and various radical initiators in boiling dioxane. Primary alcohols react similarly in boiling xylenes.

Barton-McCombie reaction - deoxygenation - alcohols - di-n-butylphosphine oxide