Ozonolysis of simple allenes leads to the formation of two carbonyl fragments and carbon monoxide.

Mechanism
Ozone inserts to the alkene by 1,3-dipolar cycloaddition to form the primary ozonide, which is highly unstable and undergoes retro 1,3-dipolar cycloaddition to form the carbonyl compound and a carbonyl oxide (Scheme 3). The carbonyl oxide, which has a dipole undergoes 1,3-dipolar cycloaddition with aldehyde to form the ozonide. The latter reacts with oxidizing or reducing agent to give the desired product.

Scheme 3

1.6.1.4 Griesbaum Cross-Ozonolysis

The O-alkyl ketone oxime was ozonide in presence of an added carbonyl compound to give the cross-ozonide product. This reaction was discovered in 1995 by Karl Griesbaum and co-workers and hence called Griesbaum cross-ozonolysis reaction.

This reaction provides a widely applicable synthesis of both symmetrical and unsymmetrical tetrasubstituted ozonides that are otherwise generally inaccessible by common ozonolysis.