Thiophilic addition of organolithiums to trithiocarbonate oxides (sulfines)

Self‐Assembly of a Trithioorthoformate‐Capped Cyclophane and Its Endohedral Inclusion of a Methine Group

“…These signals typically range between 5.3-4.1 ppm. [18][19][20] Such as hift is reminiscent of Scheme2.The desulfurization of 2 to form 4 (top left);2,8,17-trithia[4 5,12 ]- [9]metacyclophane [14] 5 (top right)a nd 1 HNMR spectrumo f4 (bottom).…”

Organosilane-Induced Synthesis and Functionalization of Sulfur-Containing Compounds

“…The reaction can also be conveniently extended to other types of sulfines, such as those of dithioesters 79a؊c [81] and trithiocarbonate 81 (Scheme 22), [82] which are converted to allyl sulfoxides 80a؊d and 82, respectively. The products obtained from dithioesters are dithioacetal monoxides, which represent useful intermediates in that they are synthetic equivalents of acyl carbanions.…”

“…The products obtained from dithioesters are dithioacetal monoxides, which represent useful intermediates in that they are synthetic equivalents of acyl carbanions. [82] It is interesting to note that aliphatic sulfines of enethiolizable dithioesters 79b,c, which can easily be prepared under strictly controlled conditions, [83] also react under the aforementioned conditions. [81] Sulfines also react with benzylsilane under the same conditions, allowing a smooth regiospecific transformation to Scheme 23.…”

“…Synthesis of benzyl sulfoxides the corresponding benzyl sulfoxides 83, 84b,c, and 85 (Scheme 23). [82,83] With the aim of introducing further reactive sites in the obtained molecules, this silicon-mediated functionalization has been extended to structurally more complex silyl derivatives such as α-hetero-substituted silyl nucleophiles.…”

An efficient one-pot access to trithiocarbonate-tethered peptidomimetics

“…For instance, they act as therapeutic agents such as inhibitors of histone deacetylases (HDAC) in the treatment of cancer, 4 and as pesticides and insecticides. 5 In organic synthesis, these compounds are employed as reversible addition fragmentation chain-transfer agents (RAFT) in radical polymerization 6 and as key precursors for the preparation of a number of compounds like trithiocarbonate-S-oxides, 7 thiols, 8 olefins, 9 thioacetates, 10 and derivatives of dicarbonyldithiocarboxylate. 11 They have also been employed as a protection for thiol functionality 12 and as useful compounds in the growing arsenal of nanotechnology in surface and colloidal science.…”