A. Menzek, A. Altundas
Dec 25, 2006
Citations
0
Influential Citations
8
Citations
Journal
Tetrahedron
Abstract
Abstract 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.