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Synlett 2000; 2000(1): 89-91
DOI: 10.1055/s-2000-6467
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Facile Iodination of Terminal Acetylenes by Anodic Oxidation in the Presence of NaI

Ikuzo Nishiguchi* , Osami Kanbe, Kotaro Itoh, Hirofumi Maekawa
  • *Department of Chemistry, Nagaoka University of Technology, 1603-1, Kamitomioka-cho, Nagaoka, Niigata 940-2188, Japan; Fax + 81-258-47-9300; E-mail: nishiiku@vos.nagaokaut.ac.jp
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Publication Date:
31 December 2000 (online)

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Electrochemical oxidation of terminal acetylenes using a divided cell in the presence of NaI as a supporting electrolyte in MeOH brought about the efficient formation of the corresponding 1-iodoacetylenes. On the other hand, use of LiCl instead of NaI under the similar conditions resulted in exclusive formation of the corresponding 1,1-dichloro-2,2-dimethoxy compounds in good yields.

terminal acetylene - 1-iodoacetylene - sodium iodide - anodic iodination - 1,1-dichloro-2,2-dimethoxy compounds - lithium chloride