K. Griesbaum et V. Ball, OZONIDE FORMATION BY TRANSANNULAR CYCLOADDITION BETWEEN A CARBONYL OXIDE AND A CARBONYL GROUP, Tetrahedron letters, 35(8), 1994, pp. 1163-1164
Ozonolysis of bicyclo[10.3.0]pentadec-1(12)-en-13-one (9a) on polyethy
lene gave the corresponding ozonide 11a. The structure of the labile o
zonide was proved by its transformation into the stable O-methyl oxime
11b, and by independent synthesis of 11b by ozonolysis of the O-methy
l oxime of 9a.