The regioselective generation of arynes from polyhalogenobenzenes. An improved synthesis of syn- and anti-1,4,5,8,9,12-hexahydro-1,4

5,8:9,12-triepoxytriphenylene

Francisco Raymo, Franz H. Kohnke, Francesca Cardullo, Ulrich Girreser, J. Fraser Stoddart

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The halogenated benzenes, 1,2,4,5-tetrabromobenzene 6, hexabromobenzene 9, p-dichlorotetrabromobenzene 11, and 1,2-dibromo-4,5-dichlorobenzene 12, were investigated as 1,3-bis-, 1,4-bis-, and 1,3,5-tris-aryne precursors by using alkyllithiums and alkali metal amides as the metalating reagents. The arynes were trapped in Diels-Alder reactions with furan as the diene. The title compounds 3a/b are now readily available in two steps in 7% overall yield from 1,2,4,5-tetrabromobenzene 6.

Original languageEnglish
Pages (from-to)6827-6838
Number of pages12
JournalTetrahedron
Volume48
Issue number33
DOIs
StatePublished - Jan 1 1992
Externally publishedYes

Fingerprint

Alkali Metals
Cycloaddition Reaction
Benzene
Amides
1,2,4,5-tetrabromobenzene
furan
hexabromobenzene
4-dichlorobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The regioselective generation of arynes from polyhalogenobenzenes. An improved synthesis of syn- and anti-1,4,5,8,9,12-hexahydro-1,4 : 5,8:9,12-triepoxytriphenylene. / Raymo, Francisco; Kohnke, Franz H.; Cardullo, Francesca; Girreser, Ulrich; Stoddart, J. Fraser.

In: Tetrahedron, Vol. 48, No. 33, 01.01.1992, p. 6827-6838.

Research output: Contribution to journalArticle

Raymo, Francisco ; Kohnke, Franz H. ; Cardullo, Francesca ; Girreser, Ulrich ; Stoddart, J. Fraser. / The regioselective generation of arynes from polyhalogenobenzenes. An improved synthesis of syn- and anti-1,4,5,8,9,12-hexahydro-1,4 : 5,8:9,12-triepoxytriphenylene. In: Tetrahedron. 1992 ; Vol. 48, No. 33. pp. 6827-6838.
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abstract = "The halogenated benzenes, 1,2,4,5-tetrabromobenzene 6, hexabromobenzene 9, p-dichlorotetrabromobenzene 11, and 1,2-dibromo-4,5-dichlorobenzene 12, were investigated as 1,3-bis-, 1,4-bis-, and 1,3,5-tris-aryne precursors by using alkyllithiums and alkali metal amides as the metalating reagents. The arynes were trapped in Diels-Alder reactions with furan as the diene. The title compounds 3a/b are now readily available in two steps in 7{\%} overall yield from 1,2,4,5-tetrabromobenzene 6.",
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