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Synthesis 1993; 1993(1): 65-66
DOI: 10.1055/s-1993-25795
short paper
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A Chemoselective Synthesis of Functionalized 1,4-Alkadiynes (Skipped Diacetylenes)

M. A. Lapitskaya* , L. L. Vasiljeva, K. K. Pivnitsky
  • *Institute of Experimental Endocrinology, National Endocrinology Scientific Centre RAMS, Moskvorechje 1, Moscow 115 522, Russia
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Publication Date:
17 September 2002 (online)

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A convenient synthesis of 1,4-alkadiynes involving condensation of 1-heptyne, 2-propyn-1-ol or methyl 5-hexynoate with propargylic tosylates or chlorides in the presence of copper(I) iodide, sodium iodide and potassium carbonate is described. Due to the mildness of the conditions the method tolerates the presence of various sensitive functional groups in the reacting components.