65185-90-2Relevant academic research and scientific papers
Flow cell electrosynthesis of phenylhydroxylamines. In situ reaction with arenesulfonyl chlorides. A convenient route to arenesulfinic acids synthesis.
Moinet, C.,Raoult, E.
, p. 214 - 221 (2007/10/02)
First, electrosyntheses of phenylhydroxylamines in a flow cell fitted with porous cathode and two counter-electrodes are described.Good yields are attained when electrolyses are performed in buffered aqueous organic or aqueous media.Reaction between p-toluenesulfonyl chloride and N-(3-chloro-4-methylphenyl)hydroxylamine, at the outlet of the cell, leads to a N-sulfonylated phenylhydroxylamine (N-addition); hydrolysis of this latter occurs in aqueous basic media to give the corresponding nitrosobenzene and sodium p-toluenesulfinate.As a result, some arenesulfinic acids have been directly obtained after reaction of arenesulfonyl chloride with sodium salt of 3-hydroxylaminobenzoate and 3-hydroxylaminobenzenesulfonate in aqueous phosphate buffer (pH 7).Next, an examination of the reaction of p-toluenesulfonyl chloride with phenylhydroxylamine in organic solvent, in the presence of triethylamine or of sodium carbonate, shows the importance of experimental conditions to control N-addition or O-addition.Addition of some arenesulfonyl chlorides to phenylhydroxylamine, in ether or dichloromethane containing sodium carbonate, gives only the N-sulfonylated phenylhydroxylamines.These compounds lead to nitrosobenzene and arenesulfinate anions in aqueous basic media.Aliphatic or aromatic sulfinic acids can be prepared in this way.
