Chemoselective Oxidation of Carbon-Carbon Double or Triple Bonds to 1,2-Diketones with DMSO-Based Reagents

Mehman S. Yusubov; Victor D. Filimonov; Valentina P. Vasilyeva; Ki-Whan Chi

doi:10.1055/s-1995-4094

Synthesis 1995; 1995(10): 1234-1236
DOI: 10.1055/s-1995-4094

short paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

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

PDF (191 kb)