Tetrahedron p. 5753 - 5764 (1994)
Update date:2022-08-03
Topics:
Atasoy, Basri
Bayramoglu, Fatma
Hoekelek, Tuncer
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.CoTTP (Cobalt(II)tetraphenylporphyrin) catalyzed rearrangement of epoxy-endoperoxide gave hydroxy-aldehyde (13) which was oxidized into dialdehyde (14).
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Doi:10.1021/jo00091a007
(1994)Doi:10.1021/ja411429b
(2014)Doi:10.1021/om00020a008
(1994)Doi:10.1016/j.tetlet.2014.01.038
(2014)Doi:10.1016/j.tetlet.2014.01.101
(2014)Doi:10.1039/c39940001247
(1994)
