A novel hydrocarbon, 8,10-dimethylidenetricyclo[7.1.1.0(2,7)]undeca-2,4,6-triene: Synthesis of benzopinane skeleton via Di-pi-methane rearrangement of benzonorbornadiene system

Altundas A., Akbulut N., Balci M.

HELVETICA CHIMICA ACTA, vol.81, no.5, pp.828-836, 1998 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 81 Issue: 5
  • Publication Date: 1998
  • Doi Number: 10.1002/hlca.19980810504
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.828-836
  • Middle East Technical University Affiliated: No

Abstract

The [4 + 2] cycloadduct 17 of 2,3-dimethylidene-1,2,3,4-tetrahydro-1,3-methanonaphthalene and 4-phenyl-4H-1,2,4-triazole-3,5-dione (PTAD) was subjected to a tripler-sensitized di-pi-methane rearrangement. Hydrolysis of the resulting urazol 18 gave the hydrocarbon 7. Hydrolysis of 18 at lower base concentrations led to isomeric stable semicarbazides 24 and 25, which were submitted NiO2 or MnO2, oxidation, to give the target compound 7, and oxidation products 26 and 27.