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, vol.49, no.15, pp.1938-1946, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Review
  • Volume: 49 Issue: 15
  • Publication Date: 2019
  • Doi Number: 10.1080/00397911.2019.1611858
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1938-1946
  • Keywords: 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 University Affiliated: Yes

Abstract

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.