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Reactions of some 2-aminophenyl- and 2- and 4-nitrophenyl sulfones in aqueous sodium hydroxide solution

 

作者: K. B. Shaw,   R. K. Miller,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1970)
卷期: Volume 48, issue 9  

页码: 1394-1403

 

ISSN:0008-4042

 

年代: 1970

 

DOI:10.1139/v70-230

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

When 2-aminophenylsulfonylacetic acid (3) was heated under reflux in an excess of dilute sodium hydroxide solution, the only product identified was 2-methylsulfonylaniline (6). When 2-nitrophenyl-sulfonylacetic acid was treated under the same conditions, the major products identified were 2-methyl-sulfonylnitrobenzene (7), 2-nitrophenol (8), and orthanilic acid (13); minor products of this reaction were6and 3-methylsulfonyl-3′-nitro-4-amino-4′-hydroxybiphenyl (12). The same products were obtained although the yields were different when7was boiled with alkali, but the reaction of 4-methylsulfonyl-nitrobenzene (15) with alkali was less complex and 4-nitrophenol (16) was the only major product. The biphenyl12was also formed in small yield whenN-(2-methylsulfonylphenyl)hydroxylamine (19) was treated with alkali and its formation in these reactions was investigated in detail. It was concluded that12arises from7and19, but it could also be prepared from19and 2-chloro- or better, 2-fluoronitrobenzene, in alkaline solution, and based on all these observations, a mechanism for its formation is suggested. The genesis of the various other products is also discussed. Reference is made to the infrared spectra of sulfones.

 

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