Reactions of 3,10-epoxycyclo[10.2.2.0 2,11.0 4,9]hexadeca-4,6,8,13-tetraene: a new intramolecular 1,5-oxygen migration

Bromination of 3,10-epoxycyclo[10.2.2.0 2,11.0 4,9]hexadeca-4,6,8,13-tetraene gave 13-bromo-11-oxapentacyclo[8.7.0.0 2,4.0 12,17]heptadeca-4,6,8-triene-3-ol, 12-bromo-1,2,3,4-tetrahydro-1,4-ethano-antracen-11-ol, 13-hydroxy-3,14-dibromotetracyclo[10.2.2.0 2,11.0 4,9]hexadeca-2,4,6,8,10-pentaene, and...

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Bibliographic Details
Published in:Tetrahedron 2006-12, Vol.62 (52), p.12318-12325
Main Authors: Menzek, Abdullah, Altundaş, Aliye
Format: Article
Language:English
Subjects:
Aromatization
Bromination
Epoxidation
Epoxide
Naphthyne
Oxygen migration
Rearrangement
Reduction
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Summary:Bromination of 3,10-epoxycyclo[10.2.2.0 2,11.0 4,9]hexadeca-4,6,8,13-tetraene gave 13-bromo-11-oxapentacyclo[8.7.0.0 2,4.0 12,17]heptadeca-4,6,8-triene-3-ol, 12-bromo-1,2,3,4-tetrahydro-1,4-ethano-antracen-11-ol, 13-hydroxy-3,14-dibromotetracyclo[10.2.2.0 2,11.0 4,9]hexadeca-2,4,6,8,10-pentaene, and 13-hydroxy-3,10,14-tribromotetracyclo[10.2.2.0 2,11.0 4,9]hexadeca-2,4,6,8,10-pentaene by cleavage of the carbon–oxygen bonds and intramolecular 1,5-migration of the oxygen atom of 1,4-epoxide. Reactions of epoxide 14,18-dioxahexacyclo[10.3.2.1 3,10.0 2,11.0 4,9.0 13,15]octadeca-4,6,8-triene obtained from 3,10-epoxycyclo[10.2.2.0 2,11.0 4,9]hexadeca-4,6,8,13-tetraene gave also similar products, in acidic media. Compound 3,10-epoxycyclo[10.2.2.0 2,11.0 4,9]hexadeca-4,6,8,13-tetraene was converted into tetracyclo[10.2.2.0 2,11.0 4,9]hexadeca-2(11),3,9-triene in two ways. The reactions, especially intramolecular oxygen migration, are discussed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.10.012