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

GUNBAS D., ALGI F., Hokelek T., WATSON W., BALCI M. N.

TETRAHEDRON, cilt.61, sa.47, ss.11177-11183, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 61 Sayı: 47
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.tet.2005.09.019
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.11177-11183
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.