Evidence for the intermediacy of an alkyne rather than an allene in the base-induced reaction of 3-bromo-6,7-benzobicyclo[3.2.1]octa-2,6-diene

TÜMER F., TAŞKESENLİGİL Y., BALCI M.

TETRAHEDRON, cilt.55, sa.35, ss.10771-10778, 1999 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 55 Sayı: 35
  • Basım Tarihi: 1999
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.10771-10778
  • Atatürk Üniversitesi Adresli: Evet

Özet

In order to reveal the real intermediate in the base-promoted reaction of 1, 2-methyl derivative 16 has been synthesized and its HBr elimination reaction studied. Reaction of 16 with potassium t-butoxide did not form the corresponding allene intermediate 17 under the same reaction conditions as described for 1. Under more drastic conditions exocyclic diene 18 was formed, These results provide evidence for the intermediacy of the alkyne 3 in the base-promoted reaction of 1. (C) 1999 Published by Elsevier Science Ltd. All tights reserved.