Collect. Czech. Chem. Commun. 1983, 48, 1048-1056

1,3-Dipolar cycloaddition of C-benzoyl-N-phenylnitrone to oxanorbornadiene and oxanorbornene derivatives; endo-exo and site selectivity

Lubor Fišera, Jaroslav Kováč, Juraj Patúš and Dušan Pavlovič

Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava


C-Benzoyl-N-phenylnitrone (Ia) and C,N-diphenylnitrone (Ib) react with 2,3-dimethoxycarbonyl-7-oxabicyclo[2,2,1]heptadiene (II) to give endo- and exo-adducts at both the substituted double bonds. The endo-exo and site selectivity of 1,3-dipolar cycloaddition is discussed. Cycloadditions of the nitrones Ia and Ib to 5,6-dimethoxycarbonyl-7-oxabicyclo[2,2,1]heptene and 2,3-dimethoxycarbonyl-7-oxabicyclo[2,2,1]-2-heptene are also described.