STABILITY AND NITROSATION EFFICIENCY OF SUBSTITUTED N-METHY-N-NITROSOBENZENESULFONAMIDES

A series of substituted N-methyl-N-nitrosobenzenesulfonamides [2,4,6-( CH3)(3), 4-CH3O, 4-CH3, 4-Cl and 4-NO2] were synthesized. All of them transfer their nitroso group to N-methylaniline in a quantitative mann er, the more reactive being those substituted with electron-withdrawin g groups, thus resembling some of the known alkyl nitrites. Studies of their acid denitrosation and base-catalysed hydrolysis demonstrated t hat the nitrosobenzene-sulfonamides are fairly stable in aqueous media between pH 2 and 11. Their relative stability in aqueous media togeth er with their ability to transfer the nitroso group to nucleophiles su ggest their use as excellent alternatives to alkyl nitrites in both ne utral and basic media. (C) 1998 John Wiley & Sons, Ltd.