A CONCISE SYNTHESIS OF THE 2,3-DIMETHYLENE-1,4-METHANO-1,2,3,4-TETRAHYDRONAPHTHALENE AND ITS REACTION WITH SINGLET OXYGEN
TETRAHEDRON, cilt.50, sa.19, ss.5753-5764, 1994 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 50 Sayı: 19
- Basım Tarihi: 1994
- Doi Numarası: 10.1016/s0040-4020(01)85643-x
- Dergi Adı: TETRAHEDRON
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.5753-5764
- Hacettepe Üniversitesi Adresli: Evet
Özet
Palladium-catalyzed carbomethoxylation of benzonorbornadiene (7) yielded dimethyl-1,4-methano-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate (9) which was transformed in three steps into 2,3-dimethylene-1,4-methano-1,2,3,4-tetrahydronaphthalene (4) in a high yield. Reaction of 4 with singlet oxygen resulted in the formation of epoxy-endoperoxide (12). X-ray crystallographic analysis demonstrated that epoxide ring is exo as methylene bridge. For the first time, the epoxy-endoperoxide formation from the ''one pot'' reaction of a diene with singlet oxygen was observed. The epoxy-endoperoxide formation mechanism was discussed. CoTPP (Cobalt(II)tetraphenylporphyrin) catalyzed rearrangement of epoxy-endoperoxide gave hydroxy-aldehyde (13) which was oxidized into dialdehyde (14).