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Synlett 1997; 1997(8): 962-964
DOI: 10.1055/s-1997-970
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Oxidative Cleavage of vic-Diols Using Copper(II) Bromide-Lithium t-Butoxide: A New Route to Unsymmetrical 1,5- and 1,6-Diketones

Tooru Fujiwara, Yumiko Tsuruta, Ko-ichi Arizono, Takeshi Takeda*
  • *Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184, Japan, Fax 81 423 88 7034; E-mail takeda-t@cc.tuat.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Unsymmetrical 1,6-diketones were obtained by the copper(II) bromide-lithium t-butoxide oxidation of 1,2-disubstituted 1,2-cyclohexanediols. The diols were easily prepared by the addition of Grignard reagents to 2-trimethylsiloxy-2-cyclohexenone followed by the hydrolysis and treatment of the resulting 2-hydroxycyclohexanones with the second Grignard reagents. Similarly, 1,5-Diketones were obtained using 2-trimethylsiloxy-2-cyclopentenone as a starting material.

diketone - vic-diol - oxidation - copper(II) bromide - lithium t-butoxide