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Mechanisms and Reactivity in Reactions of Organic Oxyacids of Sulfur and their Anhydrides

1980; Elsevier BV; Linguagem: Inglês

10.1016/s0065-3160(08)60128-8

2162-5921

John L. Kice,

Synthesis and biological activity

There are three simple organic oxyacids of sulfur: (1) sulfenic acids (RSOH), (2) sulfinic acids (RSO2H), and (3) sulfonic acids (RSO3H). Of these, the sulfonic acids are the most stable, and they and their derivatives (RSO2Y) are very commonly encountered in organic chemistry. Sulfinic acids, while often somewhat unstable thermally, have also been known for a long time. Sulfenic acids, on the other hand, are for the most part elusive reactive intermediates. Only a few, possessing special structural features, have long enough lifetimes at room temperature to allow their actual isolation. Certain derivatives of sulfenic acids, such as their acid chlorides, RSCI, are well-known, isolable, albeit reactive, compounds. In sulfur chemistry, compounds that are formally the anhydrides of the organic oxyacids of sulfur, or are mixed anhydrides derived from two oxyacids of differing oxidation state, generally have quite distinctive chemistry of their own. In this context, the chapter discusses the structure and the behavior of a particular oxyacid of sulfur highlighting the behavior of the corresponding anhydride.