Methyl alcohol, reaction with oxygen

Because the protonation of ozone removes its dipolar nature, the electrophilic chemistry of HOs, a very efficient oxygenating electrophile, has no relevance to conventional ozone chemistry. The superacid-catalyzed reaction of isobutane with ozone giving acetone and methyl alcohol, the aliphatic equivalent of the industrially significant Hock-reaction of cumene, is illustrative. 

Chloroform can be manufactured from a number of starting materials. Methane, methyl chloride, or methylene chloride can be further chlorinated to chloroform, or carbon tetrachloride can be reduced, ie, hydrodechlorinated, to chloroform. Methane can be oxychlorinated with HCl and oxygen to form a mixture of chlorinated methanes. Many compounds containing either the acetyl (CH CO) or CH2CH(OH) group yield chloroform on reaction with chlorine and alkali or hypochlorite. Methyl chloride chlorination is now the most common commercial method of producing chloroform. Many years ago chloroform was almost exclusively produced from acetone or ethyl alcohol by reaction with chlorine and alkali. 

The use of organomagnesium reagents as bases leads to complexation of the nitrile imines (e.g., 141), which has been found to have a strong effect in promoting syn selectivity in reactions with methyl 2-(l-hydroxyalkyl)acrylates via coordination of the metal atom with the alcoholic oxygen (e.g., leading to the formation of 142). Lithium complexation had little effect (78). 

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