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Synlett 1992; 1992(1): 70-72
DOI: 10.1055/s-1992-21270
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Generation and Reaction of a Transition Metal Stabilized But-2-yne-1,4-dicarbenium Ion: The First Example of the Double Nicholas Reaction

Seiichi Takano* , Takumichi Sugihara, Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan
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Publication Date:
18 September 2002 (online)

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Reaction of the dicobalt hexacarbonyl complex of 1,4-dibenzyloxybut-2-yne with nucleophiles occurs facilely at the 1,4-centers in one step in the presence of diethyl ether-boron trifluoride complex to give 1,4-difunctionalized but-2-yne complexes in excellent yield via a formal generation of transition metal stabilized but-2-yne-1,4-dicarbenium ion intermediate. The reaction is taken as the first example of the double Nicholas reaction.