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Synthesis 1995; 1995(10): 1234-1236
DOI: 10.1055/s-1995-4094
short paper
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Chemoselective Oxidation of Carbon-Carbon Double or Triple Bonds to 1,2-Diketones with DMSO-Based Reagents

Mehman S. Yusubov, Victor D. Filimonov1 , Valentina P. Vasilyeva, Ki-Whan Chi2
  • 1Department of Organic Chemistry, Tomsk Polytechnical University, Tomsk 634004, Russia, Fax +7(382)224607
  • 2Department of Chemistry, University of Ulsan, Ulsan 680-749, Republic of Korea
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Publication Date:
31 December 2000 (online)

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HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethylen)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, I2/DMSO and PdCl2/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.

chemoselective oxidation - double or triple bond - 1,2-diketone - DMSO-based reagents - Pd(II) catalyst