244 ' THE PREPABATION OF UNSYMMETRICAL BIARYLS amines: the nitroanilines, o-chloroaniline, and 0-naphthylamine, as shown in the following table. All the reactions were with benzene. COMPARISON OP YIELDS USING SODIUM HYDROXIDE AND SODIUM -ACETATE Yields Amine Aniline o-Nitroaniline wi-Nitroaniline p-Nitroaniline o-Chloroaniline m-phloroaniline p-Chloroaniline p-Toluidine p-Bromoaniline p-Anisidine p-Phenetidine jS-Naphthylamine Product Biphenyl 2-Nitrobiphenyl 3-Nitrobiphenyl 4-Nitrobiphenyl 2-Chlorobiphenyl 3-Chlorobiphenyl 4-Chlorobiphenyl 4-Methylbiphenyl 4-Bromobiphenyl 4-Methoxybiphenyl 4-Ethoxybiphenyl jS-Phenylnaphthalene NaOH 22% 21 18 26 25 25 40 22 44 25 29 16 CH 8 COONa 16% 45 45 60 38 13 35 11 12 4 11 25 The effect of various other reagents on the yield of biphenyl from diazotized aniline and benzene has been studied. The following yields of biphenyl were obtained from one mole of aniline under the conditions noted. 16
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