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
TETRAHEDRON, cilt.57, sa.35, ss.7529-7535, 2001 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 57 Sayı: 35
- Basım Tarihi: 2001
- Doi Numarası: 10.1016/s0040-4020(01)00702-5
- Dergi Adı: TETRAHEDRON
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.7529-7535
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
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.