✍ Scribed by Basri Atasoy; Fatma Bayramoğlu; Tuncer Hökelek
No coin nor oath required. For personal study only.
Palladium-catalyzed carbomethoxylation of benzonorbornadiene (7) yielded dimethyl-1.4methano-l,2.3.4-tetrahydronaphthalene-2,3-dicarboxylate (9) which was transformed in three steps into 2.3-dimethylene-l,4-methano-l.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 diins with singlet oxygen was observed. The epoxy-endoperoxide formation mechanism was discussed. CoTPP (Cobalt(rr)tetraphenylporphyrin) catalyzed rearrangement of epoxy-endoperoxide gave hydroxy-aldehyde (13) which was oxidized into dialdehyde (14).
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