Reduction of Tosylamino Acids and Related Compounds with Sodium in Liquid Ammonia; stoichiometry and products

Using an extraction procedure which permits determination of end-points, the reduction of a number of tosylamino acids, their derivatives, and model compounds with sodium in liquid ammonia has been investigated. When the molecule contains a single acidic group in addition to the tosylamino group (as in the case of the simple mono-tosylamino monocarboxylic acids) reduction proceeds with the consumption of 2 g-at. Na per tosyl group and the formation of toluene-4-sulphinic acid. If the number of acidic groups in the products is insufficient to accommodate the number of electrons consumed in the reduction, the reduction of ionisable tosylamino groups is incomplete unless an acid is added. If the number of acidic groups is higher, or excess acid is added, the sulphur-containing products include thiocresol and sulphite. This last reaction course is also observed whenever calcium is used in place of sodium. A partial interpretation of the results is offered.