Functionalization of saturated hydrocarbons. High temperature bromination of octahydropentalene. Part 19

Gunbas D., Algi F., Hokelek T., Watson W., Balci M.

TETRAHEDRON, vol.61, no.47, pp.11177-11183, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 61 Issue: 47
  • Publication Date: 2005
  • Doi Number: 10.1016/j.tet.2005.09.019
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.11177-11183
  • Keywords: bromination, hydrocarbons, pentalene, substitution, FLAME-RETARDANT, DERIVATIVES, BENZONORBORNADIENE, 1,5-CYCLOOCTADIENE
  • Middle East Technical University Affiliated: No


The synthesis and thermal bromination of octahydropentalene was studied. The reaction afforded 1a,3a,4b,6b-tetrabromo-1,2,3, 4,5,6-hexahydropentalene (14) with remarkable regio- and stereospecificity. The structure of the product was determined by H-1 and C-13 NMR data and single X-ray structural analysis. The treatment of octahydropentalene with tenfold bromine gave the octabromopentalene derivative. The formation mechanism of the products is discussed. (c) 2005 Elsevier Ltd. All rights reserved.