Synthesis of alkyl dithiocarbamates by using thiuram disulfide reagents: A metal-free C(sp3)-S bond formation

Water‐Involved C−S Bond Formation for the Synthesis of β‐Keto Dithiocarbamates from Thiuram Disulfides

“…The following plausible reaction mechanism was proposed based on experiments and relevant literatures [19] (Scheme 4). Initially, α-bromoacetophenone (1) forms complex B in the presence of CuI (A), and then B reacted with TMTD (2) to produce intermediate C in the presence of base.…”

“…Therefore, it would be still attractive to explore milder and more efficient approaches to achieve functionalized dithiocarbamates, such as β-keto dithiocarbamates. As part of our long-term interest in developing dithiocarbamates and exploring their relevant applications, [19] we wish to report an effective and practical method for the synthesis of more functionalized β-Keto dithiocarbamates by treating cheap and environmentally benign thiuram disulfide reagents with substituted α-haloacetophenones (Scheme 2).…”

Reaction Pathway and Selectivity Control of Tetraethyl Thiuram Disulfide Synthesis with NaHCO3 as a pH Regulator

“…2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) was chosen to investigate the reaction mechanism as a radical scavenger as it can capture the sulfur radical (RS·) , and often it is used to check if a reaction is a free radical reaction by excessive addition. , As no white solid, TETD, appeared during oxidation and no TETD was detected by the HPLC–MS method, the oxidation to produce TETD was suggested to be a radical reaction. Meanwhile, sodium diethyldithiosulfonic acid was detected by HPLC–MS and NaEt 2 DTCS was detected by UV–vis (an absorption peak appeared at 326 nm) in both the CO 2 and NaHCO 3 methods, which means that this kind of oxidation could happen without sulfur radical generation (Figure ).…”

“…Tetraethyl thiuram disulfides (TETDs), one of the important rubber vulcanization accelerators, can also be applied to prevent fungal diseases and treat alcoholism . In some studies, it has been used to synthesize diethyldithiocarbamates based on the instability of the disulfide bond, phosphorothioate oligonucleotides, and tetraethyl thiuram monosulfides, − and in recent years, it was found that TETD could act as an irreversible monoglyceride lipase (MGL) inhibitor to regulate the endocannabinoid system (ECS), which could hold therapeutic promise, for instance, in growth inhibition of prostate and breast cancer cells. , …”

Design and Characterization of New Dinuclear Macrocyclic Dithiocarbamate Complexes by the Preparation of a Free Ligand Derived from Isopropylamine

“…The structural organization of the resulting metal complexes is determined by these binding properties [6]. Besides their complexation behavior, dithiocarbamates have myriad applications that range over a variety of scientific subjects, such as medicine [7,8], biological systems [9], materials science [10], and analytical chemistry [2], as well as industrial applications such as rubber vulcanization [11]. This property has encouraged a growing interest in their usage in environmental applications [12] and serving as herbicides [13] and fungicides [9] in agriculture.…”