Rearrangement of unsaturated cyclic peroxides obtained by photooxygenation of 2,3-dimethylene-7-oxabenzonorbornene and 2,3-dimethylene-1,4-etheno-1,2,3,4-tetrahydronaphthalene

Ozen R., Kormali F., Balci M. , Atasoy B.

TETRAHEDRON, vol.57, no.35, pp.7529-7535, 2001 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 35
  • Publication Date: 2001
  • Doi Number: 10.1016/s0040-4020(01)00702-5
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.7529-7535


Cobalt(II) tetraphenylporphyrin (CoTPP)-catalyzed rearrangement of peroxide 11 obtained by the photooxygenation of 5 gave a mixture of epoxides 15 (or 16) and 17. However, CoTPP-catalyzed rearrangement of peroxide 20 arising by photooxygenation of 2,3-dimethylene-1,4-etheno-1,2,3,4-tetrahydronaphthalane 6 gave 1,4-etheno-1,2,3,4-tetrahydronaphtho[b]-furan 21. The different behaviour of these endoperoxides 11 and 20 is discussed in terms of ring strain and the degree of the pyramidalization of the C=C bond. (C) 2001 Elsevier Science Ltd. All rights reserved.