Thiobenzophenone

Unlike other thioketones that tend to dimerize to form rings and polymers, thiobenzophenone is quite stable, although it photoxidizes in air back to benzophenone and sulfur.

[1] Thiobenzophenone is deep blue and dissolves readily in many organic solvents.

Due to steric interactions, the phenyl groups are not coplanar and the dihedral angle SC-CC is 36°.

[1] One of the first reported syntheses of thiobenzophenone involves the reaction of sodium hydrosulfide and diphenyldichloromethane:[3] An updated method involves sulfiding of benzophenone:[4] In the above reaction scheme, a mixture of gaseous hydrogen chloride and hydrogen sulfide are passed into a cooled solution of benzophenone in ethanol.

[6] The rate of thioketones in cycloadditions is related but not limited to the size of the small HOMO/LUMO energy gap of the π-MOs of the C=S double bond.