Palladium-catalysed oxidation of alcohols with carbon tetrachloride, formation of 4,4,4-trichloro ketones from allylic alcohols and carbon tetrachlorid

Hideo nagashima, Koji Sato, Jiro Tsuii

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Abstract

Pd salts catalyse oxidation of alcohols with CCl4 in the presence of K2CO3. Primary alcohols are oxidised to esters, and secondary alcohols to ketones. CCl4 is converted to CHCl3. The reaction of allylic alcohols bearing a terminal olefinic bond with CCl4 or BrCCl3 in the presence of palladium catalyst at 110° affords 4,4,4-trichloro ketones. At 40°, simple adducts of CCl4 or BrCCl3 having a halohydrin structure are obtained, which are converted to the corresponding trichloro ketones by the catalysis of palladium. Various halohydrins are converted to ketones by Pd catalysis.

Original languageEnglish
Pages (from-to)5645-5651
Number of pages7
JournalTetrahedron
Volume41
Issue number23
DOIs
Publication statusPublished - 1985
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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