Can I read A Concise Synthesis of the 2,3-Dimethylene-1,4-methano-1,2,3,4-tetrahydronaphthalene and Its Reaction with Singlet Oxygen on EtoBox?

A Concise Synthesis of the 2,3-Dimethylene-1,4-methano-1,2,3,4-tetrahydronaphthalene and Its Reaction with Singlet Oxygen by Basri Atasoy; Fatma Bayramoğlu; Tuncer Hökelek is a Chemistry article available to read on EtoBox.

What is A Concise Synthesis of the 2,3-Dimethylene-1,4-methano-1,2,3,4-tetrahydronaphthalene and Its Reaction with Singlet Oxygen about?

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).

Who reads A Concise Synthesis of the 2,3-Dimethylene-1,4-methano-1,2,3,4-tetrahydronaphthalene and Its Reaction with Singlet Oxygen?

Author

Basri Atasoy; Fatma Bayramoğlu; Tuncer Hökelek

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1994

Language

EN

Field

Chemistry (Physical Sciences)