Iodine-induced transannular coupling of 1,6-cyclodecadiyne

Xinhong Gu, Michael Sponsler

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

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
Volume37
Issue number10
DOIs
StatePublished - Mar 4 1996

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Halogenation
Benzene
Iodine
Ether
Methanol
chlorobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Iodine-induced transannular coupling of 1,6-cyclodecadiyne. / Gu, Xinhong; Sponsler, Michael.

In: Tetrahedron Letters, Vol. 37, No. 10, 04.03.1996, p. 1571-1574.

Research output: Contribution to journalArticle

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