Synthesis of 1,7-epoxycyclononanes and 1,8-epoxycyclodecanes by β-fragmentation reactions using LTA and I2

  • Montaña Á
  • Ponzano S
N/ACitations
Citations of this article
4Readers
Mendeley users who have this article in their library.
Get full text

Abstract

The reaction of derivatives on C3 of 6-hydroxy-2,7-dimethyl-11-oxatricyclo[6.2.1.02,6]undecan-4-one with lead tetraacetate and iodine, gave, in a good yield, 1,7-epoxycyclononanes. These compounds are the result of a β-fragmentation at the level of C2-C6 respect to the tertiary hydroxyl group on C6, with an unexpected contraction from a ten to a nine-membered ring system, via a radical addition to the carbonyl group on C4. The treatment of precursors (non-functionalized on C3) with LTA and iodine produced again a β-fragmentation without any structural rearrangement, affording a typical 1,8-epoxycyclodecane system. The transformation of the carbonyl group on C4 into acetate avoided radical additions and rearrangements affording, in high yield, the corresponding cyclodecanes. By this methodology, either 1,7-epoxy-cyclononane or 1,8-epoxycyclodecane could be synthesized, in a good yield, from the same versatile precursor. © 2006 Elsevier Ltd. All rights reserved.

Cite

CITATION STYLE

APA

Montaña, Á. M., & Ponzano, S. (2006). Synthesis of 1,7-epoxycyclononanes and 1,8-epoxycyclodecanes by β-fragmentation reactions using LTA and I2. Tetrahedron Lett., 47(47), 8299–8304. https://doi.org/10.1016/j.tetlet.2006.09.103

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free