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, vol.63, no.34, pp.8151-8156, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 63 Issue: 34
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tet.2007.05.124
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.8151-8156
  • Middle East Technical University Affiliated: Yes

Abstract

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.