Collect. Czech. Chem. Commun. 1985, 50, 1971-1981

Solvent and substituent effects on rearrangement of 4-(4-X-phenyl)-2,7-dioxa-3-azabicyclo[3,3,0]oct-3-enes

Lubor Fišeraa, Marta Konopíkováa, Ladislav Štibrányia and Hans-Joachim Timpeb

a Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava, Czechoslovakia
b Department of Photochemistry, Technical University, 42 Merseburg, G.D.R


Preparation of the title compounds V is described. They give, on irradiation, the 2,3-dihydro-6H-1,3-oxazine derivatives VI as the main products besides the tetrahydrofuro[3,4-d]oxazoline derivatives VII. The VI to VII product ratio depends on the substituent bound to the aromatic residue. Polar solvents favour formation of the VI derivatives in the order Cl >H > CH3. In non-polar solvents the proportion of VII is increased. The quantum yields of the photoreaction vary within the limits from 0.006 to 0.04 (H >F > Cl > CH3 > OCH3).