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Synthesis 1995; 1995(10): 1234-1236
DOI: 10.1055/s-1995-4094
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
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Publication History
Publication Date:
31 December 2000 (online)
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