ChemInform Abstract: Preparation and Spectroscopic Characterization of Mixed Substituted Sulfonium Sulfanes.

Outsmarted by nootropics? An investigation into the thermal degradation of modafinil, modafinic acid, adrafinil, CRL‐40,940 and CRL‐40,941 in the GC injector: formation of 1,1,2,2‐tetraphenylethane and its tetra fluoro analog

“…Interestingly, the analogous dibenzhydryl disulfide has been shown to decompose on heating to yield 1,1,2,2,tetraphenylethane [56,57] and oxysulfonium salts have also been reported previously. [58][59][60] When equimolar (30-970 μM) acetonitrile solutions of modafinil or modafinil sulfide (Figure 3c) were injected separately on to the GC, the relative amount of 1,1,2,2tetraphenylethane formed, based upon peak areas, was on average approximately 90 % lower for the sulfide (Supporting Information 3), indicating the sulfoxide oxygen may promote thermal degradation by the facile formation of the oxysulfonium intermediate. The sulphur lone pairs in modafinil sulphide may less readily form a sulfonium salt intermediate with the benzhydrylium ion (Figure 3c), thus resulting in relatively lower yields of 1,1,2,2tetraphenylethane.…”