Collect. Czech. Chem. Commun. 1988, 53, 1060-1067

Cycloaddition of arylnitrile oxides to 2H,5H-1,6-benzodioxocine and related compounds

Lubor Fišeraa, Libuše Jaroškováa, Werner Schrothb, Michael Gäblerb and Peter Oraveca

a Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava, Czechoslovakia
b Department of Organic Chemistry, Martin-Luther University, 4050 Halle-Wittenberg, G.D.R.


3-Aryl-3a,4,11,11a-tetrahydroisoxazolo[5,4c]-1,6-benzodioxocines VIII were formed by a 1,3-dipolar cycloaddition of arylnitrile oxides to 2H,5H-1,6-benzodioxocine (III). The heterocycle VII afforded monoadducts IX, whereas dipolarophiles IV-VI do not yield cycloaddition products with nitrile oxides under the same reaction conditions. Irradiation of isoxazolines VIII, IX with UV light led to tarry products.