Four isomers are possible for R2S2O2, at least restricting sulfur to di- and tetravalency: (RO)2S=S, ROSSOR, RS(O)2SR, and RS(O)SOR. For the first two, the R groups are equivalent, and in the latter two they are nonequivalent. A simple example is diethylthiosulfite, (EtO)2S=S. It is also known as diethylthionosulfite. It is a stereochemically rigid on the NMR timescale to about 140 °C, somewhat similar to diethylsulfoxide. Many derivatives have been prepared from glycols. From meso-hydrobenzoin (PhCH(OH)−CH(OH)Ph), one obtains two isomers; a third isomer results from
d,
l-PhCH(OH)−CH(OH)Ph. The reaction with simple alkoxide sources with
disulfur dichloride gives the unbranched ROSSOR. They are immiscible in water, but dissolve in benzene or carbon tetrachloride. These species are less rigid than the thiosulfite esters. ==References==