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

Authors
Ozen, R Kormali, F Balci, M Atasoy, B
Citation
R. Ozen et al., Rearrangement of unsaturated cyclic peroxides obtained by photooxygenationof 2,3-dimethylene-7-oxabenzonorbornene and 2,3-dimethylene-1,4-etheno-1,2,3,4-tetrahydronaphthalene, TETRAHEDRON, 57(35), 2001, pp. 7529-7535
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
35
Year of publication
2001
Pages
7529 - 7535
Database
ISI
SICI code
0040-4020(20010827)57:35<7529:ROUCPO>2.0.ZU;2-G
Abstract
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-tetrahydronaphtha lane 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 s train and the degree of the pyramidalization of the C=C bond. (C) 2001 Else vier Science Ltd. All rights reserved.