1.6.1 Ozone
R. A. Berglund, Encyclopedia of Reagents for Organic Synthesis, John wiley and Sons, Inc., L. A. Paquette, Ed., New York, 1995, 6, 3837. |
1.6.1.1 Introduction
Ozone is triatomic oxygen species with a characteristic smell and pale blue color. It is less stable and highly reactive and slightly soluble in water but more soluble in non-polar solvents such as carbon tetrachloride.
1.6.1.2 Preparation
Ozone is prepared by passing dry oxygen through two electrode connected with AC current.
1.6.1.3 Ozonolysis
The reactions of alkenes with ozone can produce alcohols, aldehydes, ketones and carboxylic acids depending on the reaction conditions (Scheme 2-3). This degradation of alkenes with ozone
Scheme 1 |
is called ozonolysis. The reaction is performed in common solvents such as dichloromethane, methanol and acetone at -78°C. A reductive work up with Me2S or PPh3 or thiourea or zinc dust produces aldehydes and ketones, where as sodium borohydride (NaBH4) produces alcohols and the oxidative work up with H2O2 provides acids.
Examples:
Scheme 2 |