An unusual zinc-promoted reductive retro-Wagner-Meerwein rearrangement

TAŞKESENLİGİL Y., BALCI M.

TURKISH JOURNAL OF CHEMISTRY, cilt.20, sa.4, ss.335-340, 1996 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 20 Sayı: 4
  • Basım Tarihi: 1996
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.335-340
  • Atatürk Üniversitesi Adresli: Evet

Özet

Bromination and dehydrobromination of exocyclic olefin 8 resulted in the formation of bromomethylene compound 9 and Wagner-Meerwein rearrangement product 10. The dehydrobromination of 10 with potassium tert-butoxide provided the corresponding bromomethyl compound 11 in high yield. Reaction of 11 with Zn-Cu couple in methanol afforded the methyl derivative 12 and the parent olefin 8. The unusual formation mechanism of 8 has been discussed in term of a reductive retro-Wagner-Meerwein rearrangement.