Accession Number : AD0708369

Title :   REACTIONS OF SOME 2-AMINOPHENYL AND 2-AND 4-NITROPHENYL SULFONES IN AQUEOUS SODIUM HYDROXIDE SOLUTION,

Corporate Author : DEFENCE RESEARCH ESTABLISHMENT OTTAWA (ONTARIO)

Personal Author(s) : Shaw,K. B. ; Miller,R. K.

Report Date : 06 NOV 1969

Pagination or Media Count : 11

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)

Descriptors :   (*ORGANIC SULFUR COMPOUNDS, CHEMICAL REACTIONS), (*ORGANIC NITROGEN COMPOUNDS, CHEMICAL REACTIONS), ACETIC ACID, PHENOLS, AMINES, HYDROXAMIC ACIDS, CANADA

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE