ADDITION OF ARYLSULFINIC ACIDS TO N,N-DIALKYLQUINONE DIIMINES

The addition of arylsulfinates (2) to N,N-dialkylquinone diimines (1) under anaerobic conditions can result in four products. Sulfonamide 3 is produced in good yield under a variety of conditions (pH 5-9; temperature 0-50°). One of the possible sulfones (4, the 3 isomer) is found in significant amounts at pH 5-6 at room temperature and below; the 2 isomer is not found. At pH 7-9 detectable quantities of the Nʹ,Nʹ-disulfonamide (5) and p-phenylenediamine (6) are obtained from the reactions of benzenesulfinate and sulfinates with electron-donating substituents. Significantly larger amounts of 5 and smaller amounts of 3 were obtained at 0 and 50° than at 24°. The relationship of product yield to acidity is discussed in terms of the mechanisms of analogous reactions. The reported yields were obtained from the uv spectra of reaction mixture extracts by novel matrix methods involving characteristic vectors. A linear regression technique and a calibration with the spectra of pure compounds were required. The errors in yield lie in the range of 1-5% based on starting material. © 1969, American Chemical Society. All rights reserved.