Alcohols, secondary, oxidation with tetrabutylammonium

Hypochlorite ion is an effective oxidizing agent for a variety of substrates when the reactions are conducted under phase transfer conditions [13]. Tetrabutylammonium ion catalyzes the reaction of hypochlorite with benzylic alcohols in dichloromethane or ethyl acetate solution to yield alcohols and ketones. Likewise, secondary alcohols are oxidized to ketones according to equation 11.6. The results of a series of such... 

Hypochlorites are very good oxidizers of alcohols and are frequently selective enough to oxidize secondary alcohols in preference to primary alcohols see equations 288-291). Solutions of sodium hypochlorite in acetic acid react exothermically with secondary alcohols within minutes [693]. Calcium hypochlorite in the presence of an ion exchanger (IRA 900) oxidizes secondary alcohols at room temperature in yields of 60-98% [76 5]. Tetrabutylammonium hypochlorite, prepared in situ from 10% aqueous sodium hypochlorite and a 5% dichloromethane solution of tetrabutylammonium bisulfate, oxidizes 9-fluorenol to fluorenone in 92% yield and benzhydrol to benzophenone in 82% yield at room temperature in 35 and 150 min, respectively [692]. Cyclohexanol is oxidized to cyclohexanone by teit-butyl hypochlorite in carbon tetrachloride in the presence of pyridine. The exothermic reaction must be carried out with due precautions [709]. 

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