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

Abstract

Radical addition of 3-oxopropanenitriles to 1,3-butadiene derivatives promoted by (NH₄)₂Ce(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, ¹H-NMR, ¹³C-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.

Graphical Abstract

Keywords:

• Cerium(IV) ammonium nitrate
• dihydrofuran
• radical addition

Acknowledgements

Authors thank to UNAM (Bilkent University) for HRMS spectra.

Additional information

Funding

The authors are grateful to the Kocaeli University Science Research Foundation (BAP 2010/57) for financial support.