Thermal Reactions of Regioisomeric 1,2,4-Trithiolane S-Oxides.

Grzegorz Mloston, Jaroslaw Romanski, Michael L. McKee, Hans-Peter Reisenauer,  and Peter R. Schreiner

Eur. J. Org. Chem. 2010, 2132–2137. Download

The products of the gas phase pyrolysis of two regioisomeric 1,2,4-trithiolane S-oxides were collected in an argon matrix at 10 K and studied by means of spectroscopic as well as computational methods. Whereas the main products of the pyrolysis of the ‘symmetrical’ S-oxide were identified as thioformaldehyde S-oxide and thioformaldehyde S-sulfide, the ‘non-symmetrical’ S-oxide gave predominantly dithioformic acid, which exists as a mixture of s-cis and s-trans conformers. We present a rationalization of the reaction pathways including density functional theory computations.