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Synthesis 1996; 1996(5): 589-590
DOI: 10.1055/s-1996-4265
short paper
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An Improved Procedure for the Preparation of Aryl- and Hetarylacetylenes

A. G. Mal’kina1 , L. Brandsma2 , S. F. Vasilevsky3 , B. A. Trofimov1
  • 1Institute of Organic Chemistry of the Russian Academy of Sciences, Favorsky Street 1, 664033 Irkutsk, Russia
  • 2Department of Preparative Organic Chemistry, Debye Institute, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands
  • 3Institute of Chemical Kinetics and Combustion, Russian Academy of Sciences, 630090 Novosibirsk, Russia
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Publication Date:
31 December 2000 (online)

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A number of relatively volatile acetylenes RC≡CH (R = aryl or hetaryl) have been prepared with high yields by heating a mixture of the corresponding alcohols RC≡CC(CH3)2OH and paraffin oil with small amounts of powdered potassium hydroxide in vacuum. The alcohols were obtained by Pd/Cu-catalyzed cross coupling of aryl or hetaryl halides RX (X = Br, in one case I) with the commercially available HC≡CC(CH3)2OH.

hetarylacetylenes - acetylenic alcohols - retro-Favorsky reaction - KOH-catalyzed elimination of acetone - synthesis of 2-iodo-1-methylpyrrole

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