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

✍ Scribed by Abdullah Menzek; Latif Kelebekli; Aliye Altundaş; Ertan Şahin; Fatoş Polat

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 369 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890257

✦ Synopsis

Abstract

The reaction of 1,4‐dihydro‐1,4‐epoxynaphthalene with cyclooctatetraene at 130±5° 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 undergoes a Cope rearrangement. The Cope rearrangement of this adduct was investigated in the temperature range of −85° to 100° by NMR spectroscopy.