Cycloaddition Reaction of 1,4-Dihydronaphthalene 1,4-Epoxide with Cyclooctatetraene: Cope Rearrangement in an Adduct

MENZEK A., Kelebekli L., ALTUNDAŞ A., ŞAHİN E., Polat F.

HELVETICA CHIMICA ACTA, vol.91, no.12, pp.2367-2378, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 91 Issue: 12
  • Publication Date: 2008
  • Doi Number: 10.1002/hlca.200890257
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2367-2378
  • Middle East Technical University Affiliated: Yes


The reaction of 1,4-dihydro-1,4-epoxynaphthalene with cyclooctatetraene at 130 +/- 5 degrees for 14 days gave the four products 2a,3,3a,4,9,9a,10,10a-octahydro-4,9-epoxy-3,10-ethenocyclobuta[b]anthracene (13). 25-oxanonacyclo[10,10,2,2(5,9),1(14,21),0(2,11),0(3,10),0(4,6),0(13,22),0(15,20)] heptacosa-7,15,17,19,23,26-hexaene (14), 5,5a,6,6a,6b,6c,12a,12b,12c,13,13a,14-dodecahydro-5,14-epoxy-6,13-ethenocycloocta[3',4']cyclobuta[1',2',3,4]-cyclobuta[1,2-b]anthracene (15) and bis-adduct 16. The structures of the products were determined by spectroscopic methods. It was observed that adduct 14 undeergoes a Cope rerrangement. The Cope rearrangement of this adduct was investigated in the temperature range of -85 degrees to 100 degrees by NMR spectroscopy.