Alkylation of the S-C-S linkage. Towards lipophilic mono- and ditopic heavy-metal receptors containing trithiane building blocks. Molecular structure of cis-2,4,6-tribenzyl-1,3,5-trithiane

Article abstract of DOI:10.1002/recl.19931120611

Reaction of 1,3,5-trithiane with BuLi in THF at -50 deg C, followed by reaction with an equivalent amount of alkyl halide affords the corresponding lipophilic alkyl trithianes in moderate to good yields (25 - 75 percent).Reactions with xylylene dibromides (ortho, meta, para) proceeded analogously to afford potentially ditopic ligands in reasonable overall yields (30 - 50 percent).Alkylation of 1,3,5-trithiane with excess alkyl halide results in the stereoselective formation of all-cis di- or trisubstituted trithianes.Investigation of the complexation behavior of these alkylated trithianes with Ag(1+) was done by means of conductometric titrations of AgO3SCF3 in MeCN and THF.The molecular structure of 2,4,6-tribenzyl-1,3,5-trithiane (4b) has been determined by X-ray crystallography.Crystal data for 4b: trigonal, space group R-3 with a = b = 13.2287(7), c = 20.9177(2) Angstroem, Z = 6, R = 0.030 (R_w =0.034) for 1564 reflections.