Reaction of 9-diazo-4-azafluorene with unsaturated compounds and cyclic ketones

Spiro[4-azafluorene-9,1′ cyclopropanes] were obtained by the reaction of 9-diazo-4-azafluorene with various alkenes in the form of a mixture of geometrical isomers differentiated according to the position of the substituents in the cyclopropane ring and also also according to position relative to the pyridine ring. In the reaction of 9-diazo-4-azafluorene with cyclopentanone, di(4-azafluorene-9 nyl) oxide is formed, while from its reaction with cyclohexanone, 2′-oxo-spiro[4-azafluorene-9,1′-cycloheptane] is obtained. © 1990 Plenum Publishing Corporation