Ozone
Ozone is a toxic, corrosive and unstable gas, which can decompose
spontaneously to produce oxygen. This
decomposition may be explosive at elevated temperatures or in the presence
of metals.
Ozone is produced by generating a high-voltage electrical discharge in air
or oxygen. As a strong oxidant, it reacts with various oxidizable inorganic
and organic materials. The reaction with unsaturated organic compounds gives
unstable ozonides, which can decompose violently.
Name Reactions
Recent Literature
Simple Diels-Alder-derived ketals could be selectively ozonolyzed to
monoaldehydes. An overall procedure for the preparation of a key
intermediate for porphyrin and heme synthesis is described.
D. F. Taber, K. Nakajima, J. Org. Chem., 2001,
70, 2515-2517.
The diastereoselectivity of the Griesbaum coozonolysis reaction with O-methyl
2-adamantanone oxime and 4-substituted cyclohexanones reveals that the major
tetrasubstituted ozonide isomers possess cis configurations,
suggesting a preferred axial attack of the carbonyl oxide on the
cyclohexanone dipolarophiles.
Y. Tang, Y. Dong, J. M. Karle, C. A. DiTusa, J. L. Vennerstrom, J. Org.
Chem., 2004,
69, 6470-6473.
A highly enantioselective method for catalytic reductive coupling of alkynes
and aldehydes afforded allylic alcohols with complete E/Z selectivity,
generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with
ozonolysis, this process allows the enantioselective synthesis of α-hydroxy
ketones.
K. M. Miller, W.-S. Huang, T. F. Jamison, J. Am. Chem. Soc., 2003,
125, 3442-3443.
N-Tosyl-3-halo-3-butenylamines underwent efficient Ullmann-type
coupling to afford 2-alkylideneazetidines, which could be readily converted to
the corresponding β-lactams by oxidation with O3.
H. Lu, C. Li, Org. Lett., 2006,
8, 5365-5367.
