Organic Lab Reactions 230

Organic Lab Reactions 230 - liquid for no solvent has been...

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DIAZO REACTION 225 PAGE Procedure Utilizing Sodium Diazotate ". . 247 4-Methylbiphenyl 247 Procedure Utilizing Sodium Acetate 247 o-Chlorobiphenyl 247 Procedure Utilizing a Stabilized Diazonium Salt 248 a-Phenylnaphthalene " 248 Procedure with Pyridine 248 a-, f)-, and 7-Phenylpyridine 248 Nitrosoacetylamine Reaction 248 Nitrosation by Nitrous Fumes 248 Nitrous Fumes Method 249 3-Nitrobiphenyl 249 Nitrosation by Nitrosyl Chloride 251 Preparation of Nitrosyl Chloride . . . . „. , 251 Nitrosjd Chloride Procedure 252 p-Terphenyl 252 COMPOTOIDS PREPARED BY THE REACTIONS 252 ' NATURE OF THE REACTIONS The amino group of aromatic amines can be replaced by aryl groups with the formation of unsymmetrical biaryls by two general procedures: (1) by reaction of the aryldiazo hydroxide or acetate (obtainable from the diazotized amine) with aromatic compounds, and (2) by reaction of the nitrosoacetylamine (obtainable from the acetylated amine) with aro- matic compounds. In general,- the aromatic compound must be a
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Unformatted text preview: liquid, for no solvent has been found which will not be attacked by the reactive intermediates which are formed in these reactions (p. 231). Both reactions owe their origin to Bamberger * and to Kuhling, 2 but it remained for others to develop practical procedures for utilizing them. Diazo Reaction. " As developed by Gomberg and Bachmann, 3 the first method involves the following two steps (illustrated by the prepara-tion of 4-bromobiphenyl). 1. Diazotization of an aromatic amine in the usual manner. •NHj + 2HC1 + NaNO 2-*Br— i />—N 2 + C1- + NaCl+2H 2 O 2^ Conversion of the diazonium salt to the diazohydroxide by means of alkali in the presence of a liquid aromatic compound with which the 1 Bamberger, Ber., 28, 403 (1895); 30, 366 (1897). a Kiihling, Ber., 28, 41, 523 (1895); 29, 165 (1896). 8 Gomberg and Bachmann, /. Am, Chem. Soc, 46, 2339 (1924)....
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