Iodine-induced transannular coupling of 1,6-cyclodecadiyne

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4 Scopus citations


Treatment of 1,6-cyclodecadiyne (1) with one equivalent of iodine in ether leads to regioselective transannular coupling, producing 1,5-diiodo-2,3,4,6,7,8-hexahydronaphthalene (2) in excellent yield. Solvent-incorporation products are observed in addition to 2 when the reaction is done in benzene, chlorobenzene, or methanol. Bromination of 1 gives analogous products, but the reaction is not as clean.

Original languageEnglish (US)
Pages (from-to)1571-1574
Number of pages4
JournalTetrahedron Letters
Issue number10
StatePublished - Mar 4 1996

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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