Synthesis of compounds including cyclopropane ring: Selectivity in additions

MENZEK A., Sirtbasi S., ŞAHİN E., Bayrak C., Olgun M. E., Yavari A., ...Daha Fazla

Journal of Molecular Structure, cilt.1324, 2025 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1324
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.molstruc.2024.140807
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Bromination, Cycloaddition, Cyclopropane, Spirocyclopentadiene, Strained compounds
  • Atatürk Üniversitesi Adresli: Evet

Özet

As a result of reactions such as addition, cis diolization, esterification and bromination, thirteen compounds containing spirocyclopropane were synthesized from spiro[2,4]hepta-4,6-diene (5) as the starting compound. Among these compounds, seven compounds also have an additional cyclopropane ring. A 1,3-Dipolar cycloaddition reaction of the compound obtained from cycloheptatriene-PTAD, an adduct was selectively synthesized. Additionally, bromine was selectively added to the endo-ester, resultingthe reaction of 5 and ethyl diazoacetate. The rearranged product monobromo 12 was obtained from reaction molecular bromine with compound 7, The structure of its was determined by X-ray diffraction analysis. The structure of some compounds (9, 23 and 24) were also determined by X-ray diffraction analysis. Additionally, compound 27 was obtained as endo-selectivity.