A new route to phenanthrene derivatives

Daniele Giuffrida, Franz H. Kohnke, Melchiorre Parisi, Françisco M. Raymo, J. Fraser Stoddart

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

4,5-Dimethylbenzo[1,2-c:3,4-c′]difuran (7) is a highly reactive bisdiene, which undergoes Diels-Alder reactions with a wide variety of dienophiles, including dimethyl acetylenedicarboxylate and cis-1,4-dichlorobut-2-ene, to give phenanthrene derivatives, e.g. 10 and 12, respectively, following (hydrogenation and) dehydration of the bisadducts 8 and 11, respectively. 9,10-Dimethyl-1,4:5,8-diepoxy-1,4,5,8-tetrahydro-phenanthrene (5), as a result of thermal decomposition of either (i) its bisadduct 6 with tetraphenylcyclopenta-dienone or (ii) its hydrogenated derivative 14, is a very convenient precursor of 7.

Original languageEnglish (US)
Pages (from-to)4839-4842
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number27
DOIs
StatePublished - Jul 4 1994
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Giuffrida, D., Kohnke, F. H., Parisi, M., Raymo, F. M., & Stoddart, J. F. (1994). A new route to phenanthrene derivatives. Tetrahedron Letters, 35(27), 4839-4842. https://doi.org/10.1016/S0040-4039(00)76982-6