Abstract
Organic disulfides are frequently found in many fields of science, ranging from chemistry
to materials science to biology. While symmetrical disulfides, which have the same
substitutions on the two sulfurs, are often final products, they are mostly employed
as reactants and catalysts in various reactions. In addition to their usage as catalysts,
their synthetic applications as reactants can arbitrarily be categorized into three
types: (1) surrogates for the corresponding thiols, (2) reactants for unsymmetrical
disulfides, and (3) reactants or intermediates for the other compounds. Although the
straightforward, traditional way to obtain symmetrical disulfides (RSSR) is the oxidation
of their parental thiols (RSH), they can also be obtained from non-thiolic compounds.
This short review covers representative synthetic applications of symmetrical disulfides
and their preparation methods in which the starting materials are not the corresponding
thiols.
1 Introduction
2 Synthetic Applications of Symmetric Disulfides
2.1 Surrogates for Thiols
2.2 Synthesis of Unsymmetrical Disulfides
2.3 As Reactants and Intermediates
3 Synthesis of Symmetrical Disulfides from Non-thiolic Substrates
3.1 Synthesis from Organic Halides
3.2 Synthesis from Sulfonic Acid Derivatives
3.3 Synthesis from Sulfinic Acid Derivatives
3.4 Miscellaneous
4 Conclusion
Key words
symmetrical disulfide - unsymmetrical disulfide - thiol surrogate - sulfanylation
- cross-coupling
