286-28-2Relevant academic research and scientific papers
A new, efficient, and simple method for the synthesis of thiiranes from epoxides under solvent-free conditions
Kaboudin, Babak,Norouzi, Hamid
, p. 1283 - 1285 (2004)
A simple, efficient, and new method has been developed for the synthesis of thiiranes from epoxides through a one-pot reaction of epoxides with diethyl phosphite in the presence of ammonium acetate or ammonium hydrogen carbonate/sulfur/ and acidic alumina under solvent-free conditions using microwave irradiation.
LASER INDUCED SYNTHESYS: SELECTIVE FORMATION OF CYCLOHEXENE EPISULPHIDE FROM MOLECULAR SULPHUR S8
Bertaina, C.,Fellous, R.,Lemaire, F.,Stringat, R.
, p. 5521 - 5522 (1985)
1,2-Epithiocyclohexane was obtained selectively by irradiation of a mixture of cyclohexene and sulphur with a pulsed laser (266 nm).
Preparation, characterization and application of MgFe2O4/Cu nanocomposite as a new magnetic catalyst for one-pot regioselective synthesis of β-thiol-1,4-disubstituted-1,2,3-triazoles
Eisavi, Ronak,Naseri, Kazhal
, p. 13061 - 13076 (2021/04/22)
Magnesium ferrite magnetic nanoparticles were synthesized by a solid-state reaction of magnesium nitrate, hydrated iron(iii) nitrate, NaOH and NaCl salts and then calcined at high temperatures. In order to prevent oxidation and aggregation of magnesium ferrite particles, and also for preparing a new catalyst of supported copper on the magnetic surface, the MgFe2O4was covered by copper nanoparticles in alkaline medium. Magnetic nanoparticles of MgFe2O4/Cu were successfully obtained. The structure of the synthesized magnetic nanoparticles was identified using XRD, TEM, EDS, FT-IR, FESEM and VSM techniques. The prepared catalyst was used in the three component one-pot regioselective synthesis of 1,2,3-triazoles in water. The various thiiranes bearing alkyl, allyl and aryl groups with terminal alkynes, and sodium azide in the presence of the MgFe2O4/Cu nanocatalyst were converted to the corresponding β-thiolo/benzyl-1,2,3-triazoles as new triazole derivatives. The effects of different factors such as time, temperature, solvent, and catalyst amount were investigated, and performing the reaction using 0.02 g of catalyst in water at 60 °C was chosen as the optimum conditions. The recovered catalyst was used several times without any significant change in catalytic activity or magnetic property.
Precise Synthesis of Poly(thioester)s with Diverse Structures by Copolymerization of Cyclic Thioanhydrides and Episulfides Mediated by Organic Ammonium Salts
Yue, Tian-Jun,Zhang, Ming-Chao,Gu, Ge-Ge,Wang, Li-Yang,Ren, Wei-Min,Lu, Xiao-Bing
supporting information, p. 618 - 623 (2019/01/04)
The precise synthesis of poly(thioester)s with diverse structures is still a significant challenge in the polymeric materials field. Herein, we report a novel approach to the synthesis of well-defined poly(thioester)s by the controlled alternating copolymerization of cyclic thioanhydrides and episulfides induced by simple organic ammonium salts. Both the cation and anion have strong effects on the copolymerization. [PPN]OAc ([PPN]=bis(triphenylphosphine)iminium) with a bulky cation was proven to be efficient in initiating this polymerization, yielding poly(thioester)s with a completely alternating structure, controlled molecular weight, and narrow polydispersity. The poly(thioester) obtained from succinic thioanhydride and propylene sulfide is a typical semicrystalline material, possessing a high refractive index of up to 1.78. Because it uses readily available monomers, this method is expected to open up a new route to poly(thioester)s with diverse structures and properties.
Green synthesis of thiiranes from epoxides catalyzed by magnetically separable CuFe2O4/Mg(OH)2 nanocomposite in water under benign conditions
Hassanzadeh, Shadi,Eisavi, Ronak,Abbasian, Mojtaba
, p. 240 - 255 (2019/01/30)
The magnetically separable CuFe2O4/Mg(OH)2 nanocomposite was prepared and characterized by FT-IR, XRD, SEM, EDS, and VSM techniques. The synthesized nanoparticles were used as a new and efficient heterogeneous catalyst for the conversion of various epoxides to the corresponding thiiranes with thiourea in water solvent at room temperature. The reactions were completed within 1–3.7 h to give thiiranes in 70–99% yields. The applied CuFe2O4/Mg(OH)2 nanocomposite was separated easily using an external magnet and reused for several times without any considerable loss of activity.
Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
Dong, Jun,Xu, Jiaxi
, p. 2407 - 2415 (2018/04/16)
A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
A green method for solvent-free conversion of epoxides to thiiranes using NH4SCN in the presence of NiFe2O4 and MgFe2O4 magnetic nanocatalysts
Eisavi, Ronak,Ahmadi, Fatemeh,Ebadzade, Behrooz,Ghadernejad, Seiran
, p. 614 - 624 (2017/10/03)
Nickel and magnesium ferrite magnetic nanoparticles were fabricated and applied as efficient and reusable catalysts in the solvent-free conversion of various epoxides to the corresponding thiiranes with ammonium thiocyanate under oil bath (60°C) conditions. NiFe2O4 and MgFe2O4 nanoparticles can catalyze the reactions at short times in high to excellent yields. The catalysts can also be recovered easily using an external magnetic field and be reused four times without any significant loss of activity.
Synthesis of 3-acyl-5,6-dihydro-1,4-oxathiines through ring expansion of thiiranes
Chen, Xingpeng,Xu, Jiaxi
supporting information, p. 1651 - 1654 (2017/04/04)
Synthesis of 3-acyl-5,6-dihydro-1,4-oxathiines has been achieved via reactions of thiiranes and α-diazo-β-1,3-dicarbonyl compounds under microwave and copper sulfate-assisted conditions. The current method provides a direct and simple strategy in efficient preparation of 3-acyl-1,4-oxathiines from readily available thiiranes and trans-3-acyl-5,6-dihydro-1,4-oxathiines as stereospecific products for 1,2-disubstituted cis-thiiranes. The reaction mechanism was also proposed.
Tuning diastereoisomerism in platinum(ii) phosphino- and aminothiolato hydrido complexes
Polo,Duran,Juanola,Real,Benet-Buchholz,Solà,Poater
, p. 3015 - 3028 (2017/04/14)
Chelate assisted oxidative addition of one equivalent of 2-phosphinothiols (2-(diphenylphosphino)ethanethiol 1, 1-(benzyloxy)-2-(diphenylphosphino)ethanethiol 2 and 2-(diphenylphosphino)-cyclohexanethiol 3) to tetrakis(triphenylphosphine)platinum(0) gives the corresponding hydrido[2-(phosphino-κP)thiolato-κS]triphenylphosphineplatinum(ii) complexes 8-10. Temperature variable NMR studies show that these complexes display a chemical equilibrium between the cis-P,P and trans-P,P geometries, strongly displaced toward the trans-P,P configuration (70-90%). XRD studies carried out on crystals of 8 indicate that although the two geometric isomers are present in solution, only the trans-P,P is obtained in the solid state. These results differ from the cis-P,N geometry observed for the related hydrido[2-(amino-κN)thiolato-κS]triphenylphosphineplatinum(ii) complexes 5-7 in solution. The crystal structures obtained for these aminothiolate hydrides show that the cis-P,N configuration is the only one observed in the solid state. Chelate assisted oxidative addition of one equivalent of 3-(diphenylphosphino)propanethiol 4 to tetrakis(triphenylphosphine)platinum(0) gives the resultant hydrido[3-(phosphino-κP)thiolato-κS]triphenylphosphineplatinum(ii) complex 11. This 3-phosphinothiolate hydride shows in solution only a trans-P,P geometry but presents two chelate ring conformational isomers. Density functional theory calculations have been used to explore the ligand-based stereoelectronic effects that are determinant in the different diastereoisomerism observed in these platinum(ii) hydrides (5-11).
Atom economical synthesis of di- and trithiocarbonates by the lithium: Tert -butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes
Diebler,Spannenberg,Werner
supporting information, p. 7480 - 7489 (2016/08/16)
Alkali metal alkoxides were studied as catalysts for the addition of CS2 to epoxides. A screening of several commercially available alkoxides revealed lithium tert-butoxide as an active and selective catalyst for this reaction. The influence of different reaction parameters as well as the substrate scope under optimized reaction conditions has been studied. Terminal and highly substituted epoxides as well as thiiranes were converted. In total 28 products were prepared and isolated in yields up to 95%. Notably, the reactions were performed under mild conditions without additional solvents. The regio- and stereoselectivity of the reaction has been studied e.g. by converting (R)-styrene and (R)-propylene oxide. Moreover, the test reaction was monitored by 13C NMR and a plausible mechanism for the conversion of terminal and internal epoxides is given. This proposal is in agreement with the observed regio- and stereoselectivity of the reaction.
