Incorporation of an allene unit into 1,4-dihydronaphthalene: generation of 1,2-benzo-1,4,5-cycloheptatriene and its dimerization

AZIZOGLU A., Demirkol O., KILIC T., YILDIZ Y. K.

TETRAHEDRON, cilt.63, sa.11, ss.2409-2413, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 63 Sayı: 11
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.tet.2007.01.017
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2409-2413
  • Çukurova Üniversitesi Adresli: Hayır

Özet

1-Bromo-1-fluoro-[1a,2,7,7a]-tetrahydro-1H-cyclopropa[b]naphthalene (19) has been prepared by the addition of bromolluoro-carbene to 1,4-dihydronaphthalene (18). Treatment of a solution of 19 in dry ether with MeLi afforded the tricyclic hydrocarbon 17, resulting from the intramolecular C-H insertion of carbene 16, and two dimerization products, the head-to-head 20 and head-to-tail 21 allene dimers, confirming the formation of title cycloallene 15 as a reactive intermediate. B3LYP/6-31 G(d) calculation predicts the activation barriers for insertion product 17 and allene product 15 as 3.70 and 9.52 kcal/mol, respectively. This prediction was in good agreement with our experimental results. (c) 2007 Elsevier Ltd. All rights reserved.