Abstract
The two title compounds, C8H6O2S6 and C8H6O2S4Se2, are isotypic with very similar cell parameters. The complete mol-ecules constitute the asymmetric units, despite being chemically perfectly symmetric. The most prominant differences in the metrical parameters arise from the distinct sizes of sulfur and selenium in the dichalcogenide bridges, with C-S-S-C and C-Se-Se-C torsion angles of 70.70 (5) and 68.88 (3)°, respectively. The crystal packing is determined by weak non-classical hydrogen-bonding inter-actions. One carbonyl oxygen but not the other participates in C-H⋯O inter-actions zigzagging along the b axis, forming infinite chains. This is complemented by an intra-molecular C-H⋯S inter-action and further inter-molecular C-H⋯S (C-H⋯Se) inter-actions, resulting in a three-dimensional network. The inter-actions involving the bridging chalcogenides form chains protruding along the c axis.
Highlights
The two title compounds, C8H6O2S6 and C8H6O2S4Se2, are isotypic with very similar cell parameters
Two 3-methyl-1,3-ene-dithiol-2-one moieties are linked by a dichalcogenide bridge (S22À or Se22À), which is attached to one of the ene carbon atoms, while the other ene carbon is bound to a methyl group (Figs. 1 and 2)
While related bridged 1,3-ene-dithiol-2-thione moieties are reported for disulfides and one compound in which the disulfide is part of a heterocycle with the 1,3-ene-dithiol-2-one moiety (Chou et al, 1998), no such analogues are known in the case of the diselenide bridge
Summary
Selenium- and sulfur-containing compounds play an important role in nature. Disulfide and diselenide compounds were developed as catalysts for oxidative protein folding and refolding reactions (Arai et al, 2018). Instead of the targeted products, the applied order of reactions yielded the novel disulfide and its diselenide analogue, which have potential applications in redox chemistry and as biologically interesting compounds. S—S or Se—Se moieties are formed, replacing the nBu3Sn substituents of alkene carbon atoms of two distinct and linked 1,3-ene-dithiol-2-one units. As this constitutes a substitution of a nBu3Sn functional. E74, 840–845 group, it is quite likely that this method can be applied to a variety of respective different precursors
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