Regioselective radical addition of 3-oxopropanenitriles with terminal dienes promoted by cerium(IV) ammonium nitrate and manganese(III) acetate

Hocaoglu B., YILMAZ M.

SYNTHETIC COMMUNICATIONS, cilt.49, sa.15, ss.1938-1946, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Derleme
  • Cilt numarası: 49 Sayı: 15
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1080/00397911.2019.1611858
  • Dergi Adı: SYNTHETIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1938-1946
  • Anahtar Kelimeler: Cerium(IV) ammonium nitrate, dihydrofuran, radical addition, FLUORINATED 1,3-DICARBONYL COMPOUNDS, ELECTRON-RICH ALKENES, CONVENIENT SYNTHESIS, OXIDATIVE CYCLIZATION, 3-CYANO-4,5-DIHYDROFURANS, DERIVATIVES, 2-THIENYL, AMIDES
  • Kocaeli Üniversitesi Adresli: Evet

Özet

Radical addition of 3-oxopropanenitriles to 1,3-butadiene derivatives promoted by (NH4)(2)Ce(NO2)(6) and Mn(OAc)(3) afforded 5-ethenyl-4,5-dihydrofuran-3-carbonitriles in low to good yields. These dihydrofurans were characterised by IR, H-1-NMR, C-13-NMR and HRMS spectra. All radical additions performed via CAN and Mn(OAc)(3) were occurred on the terminal double bond on dienes. A mechanism for the formation of the dihydrofurans was proposed.