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Synlett 1995; 1995(7): 745-747
DOI: 10.1055/s-1995-5076
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A One-pot Conversion of Propargylic Bromides to Allenyl-, Propargyl- and 1-Propynyllithiums

Takahiro Kanda1 , Yoshio Ando1 , Shinzi Kato1 , Nobuaki Kambe2 , Noboru Sonoda2
  • 1Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-11, Japan
  • 2Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita Osaka 565, Japan
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Publication Date:
31 December 2000 (online)

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Reaction of BuTeLi with propargylic bromides yields corresponding allenic and/or propargylic tellurides. The subsequent Li-Te exchange of the tellurides at low temperatures affords allenyl- and/or propargyllithiums. Thus formed propa-1,2-dienyllithium rearranges to 1-propynyllithium in refluxing THF. These organolithiums were trapped with carbonyl compounds to give homopropargylic and propargylic alcohols.

Li-Te exchange - propargylic bromides - propargyllithium - allenyllithium - 1-propynyllithium