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
Benzyl ether protective groups are oxidatively removed by ozone under relatively
mild conditions. Reaction products are benzoic ester, benzoic acid, and the
corresponding alcohol. Subsequent deacylation with sodium methoxide affords a
convenient debenzylation technique which has been applied to various O-benzyl
protected carbohydrates.
P. Angibeaud, J. Defaye, A. Gadelle, J.-P. Utille, Synthesis,
1985,
1123-1125.
Ozonolysis in Solvent/Water Mixtures: Direct Conversion of Alkenes to Aldehydes
and Ketones
C. E. Schiaffo, P. H. Dussault, J. Org. Chem., 2008,
73, 4688-4690.
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.
