Reactions of 3,10-epoxycyclo[10.2.2.0(2,11).0(4,9)]hexadeca-4,6,8,13-tetraene: a new intramolecular 1,5-oxygen migration


Menzek A., Altundas A.

TETRAHEDRON, vol.62, no.52, pp.12318-12325, 2006 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 62 Issue: 52
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tet.2006.10.012
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.12318-12325

Abstract

Bromination of 3,10-epoxycyclo[10.2.2.0(2,11).0(4.9)]hexadeca-4,6,8,13-tetraene gave 13-bromo-11-oxapentacyclo[8.7.0.0(2,4).0(12,17)]-heptadeca-4,6,8-triene-3-ol, 12-bromo-1,2,3,4-tetrahydro-1,4-ethano-antracen-ll-ol, 13-hydroxy-3,14-dibromotetracyclo[10.2.2.0(2,11).0(4,9)]hexadeca-2,4,6,8,10-pentaene, and 13-hydroxy-3,10,14-tribromotetracyclo[10.2.2.0(2,11).0(4,9)]hexadeca-2,4,6,8,10-pentaene by cleavage of the carbon-oxygen bonds and intramolecular 1,5-migration of the oxygen atom of 1,4-epoxide. Reactions of epoxide 14,18-dioxahexacyclo[10.3.2.1(3.10).0(2,11).0(4,9).0(13,15)] octadeca-4,6,8-triene obtained from 3,10-epoxycyclo[10.2.2.0(2,11).0(4,9)]hexadeca-4,6,8,13-tetraene gave also similar products, in acidic media. Compound 3,10-epoxycyclo[10.2.2.0(2,11).0(4,9)]hexadeca-4,6,8,13-tetraene was converted into tetracyclo[10.2.2.0(2,11).0(4.9)] hexadeca-2(11),3,9-triene in two ways. The reactions, especially intramolecular oxygen migration, are discussed. (c) 2006 Elsevier Ltd. All rights reserved.