Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones

Zora M., Tumay T. A., Bueyuekguengoer O.

TETRAHEDRON, cilt.63, sa.19, ss.4018-4026, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 63 Sayı: 19
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.tet.2007.03.001
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4018-4026
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

The coupling of ferrocenyl alkynes with cyclopropylcarbene-chromium complex leads to ferrocenyl-substituted 2-cyclopentenones with or without a hydroxy substituent, namely 4-cyclopentene-1,3-diones, 2-cyclobutenones, and alpha, beta-unsaturated aldehydes in varying amounts. The reaction initially produces a cyclopentadienone intermediate, then to the double bond of which, bearing a ferrocenyl group, addition of water occurs to afford hydroxy-substituted 2-cyclopentenones. In all the products, the hydroxy group ends up oc to the ferrocenyl moiety. In contrast, where no addition of water occurs, the alkenic bond is reduced to give 2-cyclopentenones. A secondary reaction product, namely 4-cyclopentene-1,3-dione, is formed by hydrolysis of the cyclopentadienome intermediates. (C) 2007 Elsevier Ltd. All rights reserved.