Bis(4-trimethylsilylphenyl) Disulfide and Bis(4-trimethylsilylphenyl) Diselenide

X = S [18546-89-9] C18H26S2Si2 (MW 362.70) X = Se [850185-96-5] C18H26Se2Si2 (MW 456.49) InChI = 1S/C18H26S2Si2/c1-21(2,3)17-11-7-15(8-12-17)19-20-16-9-13-18(14-10-16)22(4,5)6/h7-14H,1-6H3 InChIKey = RNHDNEGPJOGBBX-UHFFFAOYSA-N (reagents used as odorless replacements for diphenyl disulfide and diphenyl diselenide) Physical Data: bis(4-trimethylsilylphenyl) disulfide is a colorless solid, mp 47–48 °C (hexane), and bis(4-trimethylsilylphenyl) diselenide is a yellow solid, mp 45 °C. Preparative Methods:1 the synthesis of bis(4-trimethylsilylphenyl) disulfide 2 involves oxidation of odorless 4-trimethylsilylthiophenol 12a with odorless methyl 6-morpholinohexyl sulfoxide (MMSO)2b in the presence of hexamethyldisilazane (HMDS) (eq 1). For the diselenide, 4-trimethylsilylphenylmagnesium bromide was reacted with selenium powder to provide the organoselenium intermediate 3, which was then reduced with NaBH4 in MeOH to afford the desired diselenide 4 in 65% overall yield (eq 2). (1) (2)