High temperature bromination. Part 22: Bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalene

Demirci-Gueltekin D., Guenbas D. D., TAŞKESENLİGİL Y., BALCI M.

TETRAHEDRON, cilt.63, sa.34, ss.8151-8156, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 63 Sayı: 34
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.tet.2007.05.124
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8151-8156
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

The high-temperature bromination of 1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalene and its carboethoxy derivative was studied. Reaction of the title compound with 1 mol of bromine in refluxing carbon tetrachloride resulted in the formation of ring-opening products. In the case of the carboethoxy derivative,bromination took place both regio- and stereospecifically at the benzylic positions,the cyclopropane ring did not undergo bond cleavage. A mechanism for the formation of the products and their dehydrobromination reactions is discussed. (c) 2007 Elsevier Ltd. All rights reserved.