Collect. Czech. Chem. Commun. 1982, 47, 523-534

1,3-Dipolar cycloaddition of C-benzoyl-N-phenylnitrone with dihydrofuran derivatives. Investigation of endo-exo stereoselectivity

Lubor Fišeraa, Miloslava Dandárováa, Jaroslav Kováča, Anton Gáplovskýb, Juraj Patúša and Igor Goljerc

a Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava
b Institute of Chemistry, 816 00 Bratislava
c Laboratory of NMR Spectroscopy, Slovak Institute of Technology, 812 37 Bratislava


C-Benzoyl-N-phenylnitrone (Ia) reacts with dihydrofuran derivatives (2,3-dihydro- and 2,5-dihydrofuran, 2,5-dimethoxy- and 2,5-diacetoxy-2,5-dihydrofuran) via 1,3-dipolar cycloaddition to give diastereoisomeric pair of exo- and endo- cycloadducts. The endo-exo stereoselectivity of the reaction is discussed. Cycloaddition of C,N-diphenylnitrone (Ib) with 2,3-dihydrofuran is also described. The cycloaddition kinetics have been studied with the nitrone Ia and non-substituted dihydrofurans.