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

Menzek A., Altundas A.

TETRAHEDRON, cilt.62, sa.52, ss.12318-12325, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 62 Sayı: 52
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1016/j.tet.2006.10.012
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.12318-12325
  • Anahtar Kelimeler: aromatization, bromination, epoxide, epoxidation, naphthyne, oxygen migration, rearrangement, reduction, HIGH-TEMPERATURE BROMINATION, AROMATIC-COMPOUNDS, DERIVATIVES, REDUCTION, REARRANGEMENT, NAPHTHALENE
  • Gazi Üniversitesi Adresli: Evet

Özet

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-ll-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. (c) 2006 Elsevier Ltd. All rights reserved.