Search results

Search for "radical cyclization" in Full Text gives 76 result(s) in Beilstein Journal of Organic Chemistry.

Do α-acyloxy and α-alkoxycarbonyloxy radicals fragment to form acyl and alkoxycarbonyl radicals?

  • Dennis P. Curran and
  • Tiffany R. Turner

Beilstein J. Org. Chem. 2006, 2, No. 10, doi:10.1186/1860-5397-2-10

Graphical Abstract
  • us to suggest that some radicals in the Wille cascade progress to products by oxidation or group transfer rather than β-fragmentation. Results and Discussion We choose to generate the candidate radicals for fragmentation by a radical cyclization rather than by a standard atom or group abstraction
  • radical cyclization of enol ether 11a with tributyltin hydride (0.1 M) followed by chromatographic purification provided 14a in 95% yield as an inseparable 1:2 mixture of exo and endo isomers. Likewise, cyclization of enol ester 11b provided a 1:2 mixture of 14b-exo and 14b-endo in 68% isolated yield. The
  • concentrations, complete conversion of 11b was observed and reduced product 14b was formed in good yield. None of the directly reduced product 18b was observed even at the highest concentration, indicating that the intermediate radical cyclization is fast (kC > 106 s-1). Negligible amounts of ketone 15 (≤ 2
PDF
Album
Supp Info
Full Research Paper
Published 25 May 2006
Other Beilstein-Institut Open Science Activities