An unusual thioketal formation: Attempted synthesis of 2,3-dibromo-6,7-benzobicyclo[3.2.1]octa-2, 6-diene

TAŞKESENLİGİL Y., BALCI M.

Tetrahedron, cilt.51, sa.29, ss.7993-7998, 1995 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 51 Sayı: 29
  • Basım Tarihi: 1995
  • Doi Numarası: 10.1016/0040-4020(95)00414-4
  • Dergi Adı: Tetrahedron
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.7993-7998
  • Atatürk Üniversitesi Adresli: Evet

Özet

Treatment of 8 with 2 equiv. of NBS gave tetra bromide 9 which was converted to the corresponding unsaturated ketone 7. Reaction of 7 with 1,2-ethanedithiol produced the unusual thioketal 14 besides normal ketalization product 13. Reduction of 13 with Raney nickel resulted in the formation of hydrocarbon 17, instead of the expected dibromide 4.