10496-18-1Relevant articles and documents
One-pot efficient synthesis of disulfides from alkyl halides and alkyl tosylates using thiourea and elemental sulfur without contamination by higher polysulfides
Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Taghavi, Zeinab Khatoon
, p. 201 - 205 (2013)
An efficient and odorless synthesis of disulfides from alkyl halides using thiourea and elemental sulfur in the presence of sodium carbonate in wet polyethylene glycol (PEG 200) at 40 C without contamination by higher polysulfides has been developed. This procedure was then extended to preparation of disulfides from alkyl tosylates at 70 C.
A one-pot, efficient, and odorless synthesis of symmetrical disulfides using organic halides and thiourea in the presence of manganese dioxide and wet polyethylene glycol (PEG-200)
Firouzabadi, Habib,Iranpoor, Nasser,Abbasi, Mohammad
, p. 508 - 509 (2010)
Primary, secondary, tertiary, allylic, and benzylic halides are converted efficiently into symmetric disulfides in high yields using thiourea as the sulfur atom source. The reactions are odorless and are performed at 30-35 °C in wet PEG-200 using MnO2 as an oxidant.
Molecularly ordered decanethiolate self-assembled monolayers on Au(111) from in situ cleaved decanethioacetate: An NMR and STM study of the efficacy of reagents for thioacetate cleavage
Singh, Anuradha,Dahanayaka, Daminda H.,Biswas, Abhijit,Bumm, Lloyd A.,Halterman, Ronald L.
, p. 13221 - 13226 (2010)
The cleavage of decanethioacetate (C10SAc) has been studied by 1H nuclear magnetic resonance (NMR) spectroscopy and scanning tunneling microscopy (STM) imaging of in situ prepared decanethiolate self-assembled monolayers (SAMs) on Au(111). Solutions of C10SAc (46 mM) and previously reported cleavage reagents (typically 58 mM) in CD3OD were monitored at 20 °C by NMR spectroscopy. Cleavage by ammonium hydroxide, propylamine, or hydrochloric acid was not complete within 48 h; cleavage by potassium carbonate was complete within 24 h and that by potassium hydroxide or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) within 2 h. Similar cleavage rates were observed for phenylthioacetate. The degree of molecular ordering determined by STM imaging increased with increasing extent of in situ cleavage by these same reagents (2.5 mM C10SAc and 2.5 mM reagent in ethanol for 1 h, then 16 h immersion of Au/mica). Less effective cleavage reagents did not cleave the C10SAc sufficiently to decanethiol (C10SH) and gave mostly disordered SAMs. In contrast, KOH or DBU completely cleaved the C10SAc to C10SH and led to well-ordered SAMs composed of (3 × 3)R30° domains that are indistinguishable from SAMs grown from C10SH. Monolayer formation from thioacetates in the absence of cleavage agents is likely due to thiol or disulfide impurity in the thioacetates. Eliminating disulfide by using Bu 3P as a sacrificial reductant also helped to produce good molecular order in the SAM. The methods presented here allow routine growth of molecularly ordered alkanethiolate SAMs from thioacetates using reagents of ordinary purity under ambient, benchtop conditions.
One-pot synthesis of organic disulfides (disulfanes) from alkyl halides using sodium sulfide trihydrate and hexachloroethane or carbon tetrachloride in the poly(ethylene glycol) (PEG-200)
Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Moosavi, Hekmat,Saeedi, Narges
, p. 1185 - 1190 (2015)
Abstract Symmetric disulfides are produced by treating their corresponding organic halides including benzylic, allylic, primary and secondary halides with Na2S·3H2O and C2Cl6 or CCl4 in PEG-200 at room temperature in high yields.
Unexpected reactivity of the Burgess reagent with thiols: Synthesis of symmetrical disulfides
Banfield, Scott C.,Omori, Alvaro Takeo,Leisch, Hannes,Hudlicky, Tomas
, p. 4989 - 4992 (2007)
(Equation Presented) Reaction of the Burgess reagent with a series of aliphatic and aromatic thiols led to the corresponding symmetrical disulfides in high yields. No olefins were detected in the reactions of aliphatic thiols.
Distinct catalytic effect of micellar solution of sodium dodecyl sulfate (sds) for one-pot conversion of alkyl halides to disulfides via an odourless process using thiourea and mno2
Firouzabadi, Habib,Iranpoor, Nasser,Abbasi, Mohammad
, p. 698 - 702 (2010)
A novel one-pot odourless synthesis of symmetrical disulfides from their corresponding halides in aqueous mediausing thiourea and MnO2 in the presence of NaHCO3 or Na2CO3 catalyzed by micellar solution of sodium dodecyl sulfate (SDS) is described. By this method, primary, allylic and benzylic halides were converted into their corresponding disulfides in high yields.
Direct synthesis of phosphorotrithioites and phosphorotrithioates from white phosphorus and thiols
Cao, Yinwei,Huangfu, Xinlei,Lu, Guozhang,Tang, Guo,Wang, Yueqiao,Zhao, Yufen
supporting information, p. 5303 - 5309 (2020/09/17)
White phosphorus (P4) is still the major commercial P-atom source for the production of organophosphorus compounds. Conventionally, C-S-P bonds were constructed from environmentally questionable P(O)X directly or indirectly. From the green chemistry point of view, formation of C-S-P bonds from inorganic molecule P4 in an easy-to-operate and atom-economical way is essential because it will avoid the hazardous chlorination process. Only five methods for the formation of C-S-P bonds from P4 have been developed over the past 70 years. Here, the first general and high-yielding synthesis of P(SR)3 and P(O)(SR)3 involving P4 and thiols is presented. With the use of KOH or K2CO3 as a base and DMSO-toluene as a solvent, both arythiols and alkylthiols are tolerant in this transformation. The reaction is characterized by a complete conversion of white phosphorus. This operationally simple and environmentally sound reaction shows a broad scope of substrates and good functional group tolerance. Moreover, this method can be easily adapted to large-scale preparation.
Cyclic telluride reagents with remarkable glutathione peroxidase-like activity for purification-free synthesis of highly pure organodisulfides
Arai, Kenta,Osaka, Yuui,Haneda, Masahiro,Sato, Yuumi
, p. 3647 - 3655 (2019/07/22)
Monoamino cyclic tellurides with a five- or six-membered ring structure and their derivatives were developed as a new class of catalyst for the oxidation of organothiols to organodisulfides in a glutathione peroxidase-like catalytic reaction. Quantitative conversion and high reaction rate were achieved by performing the reaction in an organic-aqueous segmented microflow system. Importantly, the process circumvented product purification, which is a major limitation of current organodisulfide synthetic methods.
Conversion of organic halides to disulfanes using KCN and CS2
Abbasi, Mohammad,Nowrouzi, Najmeh,Borazjani, Saeedeh Ghassab
, p. 4251 - 4254 (2017/10/11)
A sulfur transfer reagent was produced in situ upon stirring a mixture of KCN and CS2 in DMF at r.t. for 15 min, which after heating with an alkyl halide or aryl halide and CuI gave the corresponding symmetric dialkyl or diaryl disulfide, respectively, in high to excellent yields.
