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.
One-pot conversion of alkyl halides to organic disulfides (disulfanes) using thiourea and hexamethyldisilazane (HMDS) in DMSO
Abbasi, Mohammad,Jabbari, Arida
, p. 81 - 86 (2016)
A practical method to synthesize symmetric disulfides from alkyl halides has been developed. Using this procedure primary, secondary, benzylic and allylic disulfides were prepared by treating the corresponding alkyl halides with thiourea and HMDS in DMSO at 50 °C within 10-24 h in high yields.
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.
Water effects on SmI2 reductions: A novel method for the synthesis of alkyl thiols by SmI2-promoted reductions of sodium alkyl thiosulfates and alkyl thiocyanates
Zhan, Zhuang-Ping,Lang, Kai,Liu, Feng,Hu, Li-Ming
, p. 3203 - 3208 (2004)
Water as a cosolvent has significant improving effect on the reductivity of SmI2 in the reduction of sodium alkyl thiosulfates and alkyl thiocyanates. A new method for synthesis of alkyl thiols by SmI 2/THF/H2O system has been developed.
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.
Direct synthesis of disulfides from alkyl halides using thiourea and CCl4 in glycerol
Abbasi, Mohammad,Khalili, Dariush
, p. 1425 - 1430 (2015)
Abstract Dialkyl disulfides were obtained on the basis of the reaction of alkyl halides and thiourea in the presence of CCl4 and Et3N. This procedure enables the odorless and one-pot synthesis of disulfides by employing cheap, easy-to-handle and readily available reagents and substrates in wet glycerol.
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.
The synthesis of symmetrical disulfides by reacting organic halides with Na2S2O3·5H2O in DMSO
Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Saeedi, Narges
, p. 89 - 92 (2016)
A one-pot, and scalable method to prepare symmetric disulfides from their corresponding primary, secondary, allylic, and benzylic halides has been developed. In this method, a disulfide is synthesized by reacting an alkyl halide with Na2S2O3·5H2O at 60-70 °C in DMSO.
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.
Graphene Oxide-Assisted One-Pot and Odorless Synthesis of Symmetrical Disulfides Using Primary and Secondary Alkyl Halides (Tosylates) and Thiourea as Sulfur Source Reagent
Khalili, Dariush
, p. 1727 - 1734 (2015)
Graphene oxide is described as a heterogeneous oxidant for the synthesis of symmetrical disulfides through the in situ generation of thiols from primary and secondary alkyl halides (tosylates) and thiourea in wet acetonitrile. A variety of alkyl halides and alkyl tosylates can be converted to corresponding disulfides in good to excellent yields. This strategy is free of foul-smelling thiols.
