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, cilt.57, sa.35, ss.7529-7535, 2001 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 57 Konu: 35
  • Basım Tarihi: 2001
  • Doi Numarası: 10.1016/s0040-4020(01)00702-5
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.7529-7535

Özet

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.