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This methodology is mild and efficient and is compatible with several functional groups other than the alcohol.Substrates with methoxy-substituted aromatic rings are subjected to the TEMPO/TCCA oxidation, but surprisingly the reaction affords only the corresponding aldehydes (Table 1, entries 7 and 8). Unexpectedly, this procedure failed in the oxidations of unsaturated alcoholsas well. Contrary to what was observed carrying out the oxidation in the absence of water, the treatment of unsaturated alcohols with 2 equiv of trichloroisocyanuricacid and catalytic TEMPO, under the present conditions,proceeded to the corresponding carboxylic acid and to the contemporary addition to the double bond. The oxidation of trans-cinnamic alcohol furnished in fact (2RS,3SR)-2,3-dichloropropionic acid. The amount of chlorinationreaction is diminished operating with equimolar amounts of TCCA, but in this case the rate of the reaction is very reduced. To determine if this behavior was general for the double bond, we carried out the reaction with (E)- 1,1-diethoxy-3-phenyl-2-propene under the same condi- tions. After complete conversion of the alkene, (2RS,3SR)- 1,1-diethoxy-2,3-dichloro-3-phenylpropane was obtained quantitatively. |
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