Diels-Alder reactions: The effects of catalyst on the addition reaction

Yilmaz O., Kus N. S., Tunc T., ŞAHİN E.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1098, ss.72-75, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1098
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.molstruc.2015.06.012
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.72-75
  • Atatürk Üniversitesi Adresli: Evet

Özet

The reaction between 2,3-dimethyl-1,3-butadiene and dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate is efficiently achieved with small amounts of catalyst, i.e. phenol, AcOH, nafion, and beta-cyclodextrin. Exo-diastereoselective cycloaddition reactions were observed both without catalyst and different catalysts for 48 days. As a result, different products (tricyclicmolecule 5, retro-Diels-Alder product 6, and oxidation product 7) were obtained with different catalysts. In addition, we synthesized Diels-Alders product 8 and tricyclocyclitol 10 via Diels-Alder reaction. The structures of these products were characterized by H-1 NMR, C-13 NMR, MS and IR spectroscopy. (C) 2015 Elsevier B.V. All rights reserved.