I. Shimao
Aug 6, 1974
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Journal
ChemInform
Abstract
The reactions of nitrobenzenes with benzyl alcohols and aqueous alkaliLi hydroxide solution have been investigated, The yield of azoxy compounds wasaffected by the concentration of alkali hydroxide (Fig. 1 and 2). The reduction of nitrobenzenes was facilitated by.the electronwithdrawing substituents, such as nitro, carboxyl and halogen, and retarded with the electronreleasing substituents, such as hydroxyl, alkoxyl and alkyl (Table 1). A small quantity of benzylp-nitrophenyl ether was obtained as a byproduct in the reduction of p-chloro- and Pbebromo itrobenzenes. ln the reaction of P-nitroteluene, the yield of 4, 4'-azoxytoluene was poor, and the yellowish orange solid was obtained as a main product, and a small amount of azobenzene-4, 4'-dicarboxylic acid was also obtained The reactivity of substituted benzyl alcohols in the reduction of nitrobenzene increased i theorder: -CH3 -C6H5 -CH30 P-CH3 H -Cl(Table 2).