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, vol.9, no.10, pp.3776-3779, 2011 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 9 Issue: 10
  • Publication Date: 2011
  • Doi Number: 10.1039/c0ob01275k
  • Title of Journal : ORGANIC & BIOMOLECULAR CHEMISTRY
  • Page Numbers: pp.3776-3779

Abstract

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.