5943-35-1

Usage

InChI:InChI=1/C19H24N2O5/c1-13(2)8-9-21(11-17-20-16(12-26-17)19(23)25-4)18(22)14-6-5-7-15(10-14)24-3/h5-7,10,12-13H,8-9,11H2,1-4H3

Upstream product

• 75-66-1 2-methylpropan-2-thiol 
• 13686-74-3 Di-tert-butyl dithiosulfite 
• 110-06-5 di-tert-butyl disulfide 
• 4345-98-6 2,2,6,6-tetramethyl-3,5-dithiaheptane 
• 140-29-4 phenylacetonitrile 
• 117890-40-1 C₄H₉ClS₃ 
• 100-47-0 benzonitrile 
• 105-56-6 ethyl 2-cyanoacetate 
• 75-05-8 acetonitrile 
• 34256-07-0 isopropylsulfinyl chloride 
• 68409-52-9 tert-butyl hydrodisulfide 
• 10147-37-2 Isopropylsulfonyl chloride 
• 62383-66-8 tert-butylsulfenic tert-butylsulfinic dithioanhydride 
• 109-73-9 N-butylamine 

Downstream Products

• 927270-06-2 tert-butyl o-methoxycarbonylphenyl disulfide 

Relevant academic research and scientific papers

From symmetrical tetrasulfides to trisulfide dioxides: Via photocatalysis

A straightforward strategy involving photocatalysis has been established for accessing trisulfide dioxides from readily achieved symmetrical tetrasulfides. Stern-Volmer analysis and radical quenching experiments demonstrated the occurrence of a single electron transfer between the photocatalyst and sulfinic acid. Bioactive molecules such as the antihypertensive drug captopril, allicin derivatives, amino acids and terpenes were efficiently and reversibly linked through sulfur-sulfur covalent bonds. Furthermore, flow-setup syntheses of trisulfide dioxides were successfully achieved on the gram scale, indicating the great potential of the developed protocol for practical industrial applications. This journal is

Sandmeyer-Type Reductive Disulfuration of Anilines

A transition metal/ligand-free disulfuration of anilines with disulfur transfer reagents (dithiosulfonate or tetrasulfide) is reported herein. The reaction, which can be considered as a reductive disulfuration variation of the classic Sandmeyer reaction, is performed under mild conditions and exhibits broad scope across the aniline substrate and disulfur transfer reagent classes. The gram-scale synthesis of disulfides is successfully achieved through this method, rendering the approach highly valuable.

Radical Substitution Provides a Unique Route to Disulfides

Radical substitution on tetrasulfides is demonstrated to be a highly effective means to prepare unsymmetric disulfides. Alkyl and aryl radicals generated thermally or photochemically underwent substitution on readily prepared dialkyl, diaryl, and diacyl tetrasulfides to yield the corresponding disulfides in good to excellent yields. Classic and contemporary thermal and photochemical radical sources could be employed; while photoredox catalysis approaches led to either oxidation or reduction of the tetrasulfide, energy transfer photocatalysis was particularly useful. The success of the approach is driven by the thermodynamic stability of the perthiyl radicals formed upon substitution on the tetrasulfide; they simply combine under the reaction conditions to provide the starting tetrasulfide. Competition kinetic experiments reveal that alkyl radical substitution on tetrasulfides is a rapid reaction (6 × 105 M-1 s-1) that is enhanced at least 6-fold upon moving from dialkyl tetrasulfide to diacyl tetrasulfide due to favorable polar effects. This unique and versatile reaction enables introduction of disulfide moieties from a variety of radical precursors and straightforward access to hydropersulfides.

The antioxidant activity of polysulfides: It's radical!

Olefin sulfurization, wherein alkenes and sulfur are heated together at high temperatures, produces branched polysulfides. Due to their anti-wear properties, they are indispensible additives to lubricants, but are also added to other petroleum-derived products as oxidation inhibitors. Polysulfides also figure prominently in the chemistry and biology of garlic and other plants of the Allium species. We previously reported that trisulfides, upon oxidation to their corresponding 1-oxides, are surprisingly effective radical-trapping antioxidants (RTAs) at ambient temperatures. Herein, we show that the homolytic substitution mechanism responsible also operates for tetrasulfides, but not trisulfides, disulfides or sulfides. Moreover, we show that this reactivity persists at elevated temperature (160 °C), enabling tetrasulfides to not only eclipse their 1-oxides as RTAs, but also hindered phenols and alkylated diphenylamines-the most common industrial antioxidant additives. The reactivity is unique to higher polysulfides (n ≥ 4), since homolytic substitution upon them at S2 yields stabilized perthiyl radicals. The persistence of perthiyl radicals also underlies the greater reactivity of polysulfides at elevated temperatures relative to their 1-oxides, since homolytic S-S bond cleavage is reversible in the former, but not in the latter. These results suggest that olefin sulfurization processes optimized for tetrasulfide production will afford materials that impart significantly better oxidation stability to hydrocarbon-based products to which polysulfides are added. Moreover, it suggests that RTA activity may contribute to the biological activity of plant-derived polysulfides.

Oxidation of thiols to bisulfides by elemental sulfur without contamination by higher polysulfides

Dialkyl disulfides were prepared in near quantitative yield by oxidation of alkanethiols with elemental sulfur using NaOH and ethoxylated alcohols as catalysts. Tergitol 15-S-7 was one of several ethoxylated alcohols which was used. Contamination by trisulfides was essentially eliminated in the disulfide products. The ratios of disulfide to trisulfide ranged from 100/0 to 99.6/0.4 for reactions with primary and secondary alkanethiols (100% excess) such as 1-propanethiol, 1-octanethiol, 2-propanethiol, and 2-butanethiol. The process did not work for tertiary alkanethiols such as 2-methyl-2-propanethiol where the trisulfide was greatly favored.

Synthesis and decomposition of some dialkyl oxide derivatives of organotrisulfides

The isolation or detection of sulfenic sulfonic thioanhydrides 1 (e.g., 6), sulfenyl vic-disulfoxides 4 (e.g., 9, 14), and sulfinic thioanhydrides 5 (e.g., 20) has been carried out by oxidative procedures at various temperatures. The decomposition of these compounds has been investigated and is shown to be consistent with the mechanism proposed for the decomposition of trisulfide monoxides.

Use of a sacriflcial-sulfur electrode in electroorganic chemistry. V. Formation of the sequence CSSSC from S and thiols or thiolates

At a working potential of about +2.0 V (vs SCE) the carbon-sulfur electrode is a source of the electrogenerated cation S2+. In organic media, this electrophile reacts with thiols (or thiolates) to give a mixture of polysulfides of which the trisulfide is the main product. The reaction between electrogenerated Sy2- and alkyl halides is less selective. Elsevier,.

The Chemistry of Alkylsulfenyl Alkylsulfinyl Thioanhydrides. The Mechanism of Decomposition

The decomposition mechanism of alkylsulfenyl alkylsulfinyl thioanhydrides has been investigated.Although the product mixture is complex in most cases, a detailed decomposition study as well as a careful analysis of the products allows for a proposal for a general mechanism which is interesting and not simple.We find, however, that the decomposition process is consistent with that of related systems.

A simple method to prepare unsymmetrical di- tri- and tetrasulfides

Unsymmetrical di- tri- and tetrasulfides can be prepared in a one-pot reaction using SO2Cl2 SCl2 and S2Cl2 respectively to permit coupling of the appropriate thiols.

Anodic Oxidation of Di-tert-butyl Disulfide: a Facile Method for the Preparation of N-tert-Butylamides

The electrochemical oxidation of di-tert-butyl disulfide is shown to correspond to a one electron process; at 1.3 V, one carbon-sulfur bond is cleaved yielding two intermediate species; the tert-butyl cation and the radical t-BuS-S; a Ritter reaction occurs with the cation when the solvent is a nitrile and the cation dimerizes into a tetrasulfide; at a more positive potential (1.9 V) the two carbon-sulfur bonds are cleaved giving t-Bu cation and sulfur.