Organic Lab Reactions 241

Organic Lab Reactions 241 - 3 and with...

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236 THE PREPARATION OF UNSYMMETRICAL BIARYLS Arylnaphthalenes. Aryhiaphthalenes can be prepared "by replace- ment of the amino group of naphthylamines by aryl groups. a-Phenyl- naphthalene can be prepared satisfactorily only through the stabilized diazonium salt method, but /3-phenylnaphthalene is obtained readily by several procedures. A considerable number of derivatives of /3-phenyl- naphthalene have been prepared. An example is 5-nitro-6-methoxy-2- phenylnaphthalene (XII), which can be obtained in 19% yield Irom the nitromethoxy-j3-naphthylamine and benzene. From the reaction be- tween diazotized /8-naphthylamine and nitrobenzene and sodium acetate, /S-(2-nitrophenyl)-naphthalene (XIII; 14%) and jS-(4-nitrophenyl)- naphthalene (XIV; 26%) are formed. N0 2 CH 3 O XIII XIV Arylthiophenes. Thiophene couples with the diazohydroxides
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Unformatted text preview: 3 and with N-nitrosoacetylamines 1 to give phenylthiophenes and derivatives. The position taken by the aryl groups in the thiophene nucleus has not been determined in all instances. The product obtained from diazotized m-cyanoaniline and thiophene 3 in 19% yield appears to be the a deriva-tive (XV). 16 xv Arylpyridines. The amino group of aromatic amines can be replaced by the pyridyl group by the normal diazohydroxide reaction, 3 by treat-ment of the sodium diazotate in pyridine with acetyl chloride, 17 by adding the dry diazonium salt to pyridine, 18 and from the nitrosoacetyl 14 Gomberg and Bachmann, unpublished results, 1924. 17 Forsyth and Pyman, J. Chem. Soc, 1926, 2912, > Mohlau and Berger, Ber., 26, 1994 (1893),...
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