Controlled synthesis of substituted benzobasketene derivatives

Aydinli B., Celik M., Gultekin M., Uzun O., Balci M.

HELVETICA CHIMICA ACTA, vol.86, no.10, pp.3332-3341, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 86 Issue: 10
  • Publication Date: 2003
  • Doi Number: 10.1002/hlca.200390276
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.3332-3341
  • Akdeniz University Affiliated: Yes

Abstract

The addition of benzyne to trans-7,8-dibromobicyclo[4.2.0]octa-2,4-diene (6) led to the formation of dibromide 7. The dehydrobromination of 7 followed by replacement of the Br-atom with a CN substituent gave 9. Photolysis of 9 in acetone at 254 nm yielded the desired monosubstituted benzobasketene derivative 10. Bromination of monobromide 8 followed by dehydrobromination furnished the symmetrically substituted dibromo compound 15. Further bromination of 7 followed by dehydrobromination resulted in the formation of the dibromides 20 and 21. Substitution of the Br-atoms in 15, 20, and 21 with CN substituents and photolysis of the formed dicarbonitriles 16, 23, and 24 gave the target benzobasketene-dicarbonitriles 17, 25, and 26, respectively.