The thermal C-2-C-6/[2+2] cyclisation of enyne-allenes: Reversible diradical formation

Cinar M. E., VAVILALA C., FAN J., Schmittel M.

ORGANIC & BIOMOLECULAR CHEMISTRY, cilt.9, sa.10, ss.3776-3779, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 9 Sayı: 10
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1039/c0ob01275k
  • Dergi Adı: ORGANIC & BIOMOLECULAR CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3776-3779
  • İstanbul Teknik Üniversitesi Adresli: Hayır

Özet

New enyne-allenes, structurally designed toward the thermal C-2-C-6/[2 + 2] cyclisation mode, were prepared and characterised, one of them even by X-ray crystallography. The mechanism of their transformation to formal [2 + 2] cycloadducts was interrogated by trapping experiments and DFT computations. The results support a stepwise mechanism that involves the reversible formation of the C-2-C-6 diradical intermediate.