Silver(I) catalyzed oxidation of thiocarboxylic acids into the corresponding disulfides and synthesis of some new Ag(I) complexes of thiophene-2-thiocarboxylate

Recent advances in S–S bond formation

“…Aromatic thiocarboxylic acids have also been exploited for disulfane synthesis. 70 The method involves the Ag + -catalyzed oxidation of thiobenzoic and thiophene-2-carboxylic acids into the corresponding dibenzoyl disulfane under basic medium (Scheme 63).…”

Bis(N-methyl-N-phenylcarbamoyl)disulfane

“…Several other reference compounds also have an S-S bond length of 2.01-2.03 Å (Bereman et al, 1983;Rout et al, 1983;Paul and Srikrishnan, 2004;Fun et al, 2001;Raya et al, 2005;Li et al, 2006;Singh et al, 2011). The most noteworthy feature of the title compound is the torsion angle about the disulfane, which is 81.6° and as such is somewhat smaller than the theoretical optimum of 90.0° (Pauling, 1949;Torrico-Vallejos et al, 2010) that has been explained as allowing for minimal mutual repulsion of pπ orbital electron lone pairs in sulfur.…”

“…For the preparation of the title compound, and of very closely related chemical structures, see: Kobayashi et al (1973); Barany et al (1983); Schroll & Barany (1986); Schrader et al (2011). For related structures, see: CSD refcodes BOWGAV (Bereman et al, 1983), DBZOSS01&03 (Rout et al, 1983;Paul & Srikrishnan, 2004), METHUS03 (Wang & Liao, 1989), NELTUT (Fun et al, 2001), JAXPOO (Raya et al, 2005), UDALER (Li et al, 2006) and EMASIV (Singh et al, 2011). For the theoretical optimum torsion angle about the disulfane, see: Pauling (1949) Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.…”

Geometrically unprecedented 3-, 5- and 7-membered Hg(ii)–Cu(i) and Hg(ii)–Ag(i) thiolate clusters: precursors to intermetallics

“…It is well known that thiols are oxidized easily into disulfides. [16][17][18] Transition metal salts and oxides have been used as catalysts in this oxidation process. However, to the best of our knowledge, such a process has not yet been exploited to prepare intermetallic compounds.…”