ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Photochemistry of heterocycles .9. Preparation and photochemistry of substituted 7-(x-phenyl)-9,10-dioxa-8-azatricyclo[4,3,0,1(2,5)]-7-decene derivatives

Ľ. Fišera and J. Oravkin

Department of Organic Chemistry, Slovak Technical University, CS-812 37 Bratislava

Abstract:  Preparation and photolysis of isoxazolines fused with oxabicyclic heterocyclic ring have been described. The title compounds VIb—VIi were prepared by 1,3-dipolar cycloaddition of substituted benzenenitrile oxides. When X was  4-0CH₃, 4-CH₃ 4-F, 4-Cl, and 3-CI, irradiation at A =253.7 nm brought about a selective photo-rearrangement under the formation of 3-ary1-4-formyl-8-oxa-2-azabicyclo[3,2,1]-3-octene derivatives in good yields. The romo substituted derivatives gave on irradiation polymeric materials only, the nitro derivative was photostable. Quantum yields in photoreactions varied from 0.005 to 0.081, the values obtained with p-derivatives were higher than those obtained with m-derivatives. The benzo derivative VIII (0 = .58) afforded polymeric materials only.

Full paper in Portable Document Format: 396a783.pdf

Chemical Papers 39 (6) 783–794 (1985)