Synthesis of Bis-spiro Cyclopropanes Based on Meldrum's Acid by Milling

Kashani E., Pesyan N. N., Tunc T., ŞAHİN E.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, cilt.62, sa.3, ss.249-256, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 62 Sayı: 3
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1002/jccs.201400320
  • Dergi Adı: JOURNAL OF THE CHINESE CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.249-256
  • Atatürk Üniversitesi Adresli: Evet

Özet

Reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) with various solid aldehydes in the presence of cyanogen bromide and solid sodium ethoxide (EtONa) leads to the selective and efficient formation of bis-spiro cyclopropanes based on Meldrum's acid at the range of 0 degrees C to room temperature. The products were obtained in good to excellent yields. Structure elucidation is carried out by H-1 NMR, C-13 NMR, FT-IR spectroscopy, mass analyses and X-ray crystallography techniques. A possible mechanism for the formation of products is also discussed under solvent-free condition.