K. B. Shaw, R. K. Miller
May 1, 1970
Citations
0
Influential Citations
13
Citations
Journal
Canadian Journal of Chemistry
Abstract
Abstract : When 2-aminophenylsulfonylacetic acid was heated under reflux in an excess of dilute sodium hydroxide solution, the only product indentified was 2-methylsulfonylaniline. (1) When 2-nitrophenyl-sulfonylacetic acid was treated under the same conditions, the major products identified were 2-methyl-sulfonylnitrobenzene (2), 2-nitrophenol, and orthanilic acid; minor products of this reaction were (1) and 3-methylsulfonyl-3'nitro-4-amino-4'-hydroxybiphenyl. (3) The same products were obtained although the yields were different when (2) was boiled with alkali, but the reaction of 4-methylsulfonyl-nitrobenzene with alkali was less complex and 4-nitrophenol was the only major product. The biphenyl (3) was also formed in small yield when N-(2-methylsulfonylphenyl)hydroxylamine was treated with alkali and its formation in these reactions was investigated in detail. It was concluded that (3) arises from (2) and (4), but it could also be prepared from (4) and 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. (Author)