286-63-5Relevant academic research and scientific papers
Attempts to Synthesize a Thiirane, Selenirane, and Thiirene by Dealkylation of Chalcogeniranium and Thiirenium Salts
Poleschner, Helmut,Seppelt, Konrad
, p. 649 - 659 (2020/10/23)
Thiiranium salts [Ad2SR]+X? (5, 8, 9, 11, 12; X?=Tf2N? (Tf=CF3SO2), SbCl6?) and seleniranium salts [Ad2SeR]+X? (14, 16, 17, 23–25; X?=Tf2N?, BF4?, CHB11Cl11?, SbCl6?) are synthesized from strained alkene bis(adamantylidene) (1). The disulfides and the diselenides (Me3SiCH2CH2E)2 (4, 13), (tBuMe2SiCH2CH2E)2 (7, 22), and (NCCH2CH2E)2 (10, 15; E=S, Se) have been used. The thiirenium salts [tBu2C2SR]+X? (34) and [Ad2C2SR]+X? (35, 36) are prepared from the bis-tert-butylacetylene (2) and bis-adamantyl-acetylene (3) with R=Me3SiCH2CH2 and tBuMe2SiCH2CH2. Attempts to cleave off the groups Me3SiCH2CH2, tBuMe2SiCH2CH2, and NCCH2CH2 resulted in thiiranes 27, 30. No selenirane Ad2Se (33) is formed from seleniranium salts, instead cleavage to the alkene (1) and diselenide (13, 15) occurs. The thiirenium salt [Ad2C2SCH2CH2SiMe3]+Tf2N? (35) does not yield the thiirene Ad2C2S (37), the three-membered ring is cleaved, forming the alkyne (3) and disulfide (4). All compounds are characterized by ESI mass spectra, NMR spectra, and by quantum chemical calculations. Crystal structures of the salts 8, 12, 25, 17, 26, 36 and the thiiranes 27, 30 are presented.
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.
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.
A green protocol for rapid and efficient conversion of epoxides to thiiranes using alumina immobilized thiourea at solvent-free conditions
Eisavi, Ronak,Zeynizadeh, Behzad
, p. 65 - 69 (2016/01/25)
Solvent-free conversion of various epoxides to the corresponding thiiranes was carried out successfully with alumina-immobilized thiourea at room temperature. The reactions were completed within 2-9 min to give thiiranes with 83-98% yields. The utilized alumina can be reused for several times without losing its activity.
Magnetically separable nano CuFe2O4: an ef?cient and reusable heterogeneous catalyst for the green synthesis of thiiranes from epoxides with thiourea
Eisavi, Ronak,Ghadernejad, Seiran,Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh
, p. 537 - 545 (2016/10/03)
The magnetically separable nano CuFe2O4 was prepared and used as an efficient heterogeneous catalyst for conversion of various epoxides to the corresponding thiiranes with thiourea in refluxing ethanol. The reactions were completed within 34?45 min to give thiiranes in 80?95% yields. The utilized nano CuFe2O4 can be reused for several times without losing its activity.
An efficient and improved method for the conversion of oxiranes into thiiranes using graphite oxide
Mirza-Aghayan, Maryam,Molaee Tavana, Mahdieh
, p. 30 - 35 (2015/10/20)
An efficient and improved procedure has been developed for the conversion of oxiranes into thiiranes using sodium thiocyanate in the presence of graphite oxide under solvent-free conditions at an ambient temperature in excellent yields and in short reaction times.
Odourless strategy for deep eutectic solvent-mediated ring opening of epoxides with in situ generated S -alkylisothiouronium salts
Azizi, Najmedin,Yadollahy, Zahra,Rahimzadeh-Oskooee, Amin
, p. 1085 - 1088 (2014/05/20)
A general, straightforward and odourless ring-opening reaction allows the preparation of β-hydroxy sulfides from in situ generated S-alkylisothiouronium salts in urea-choline chloride-based deep eutectic solvent (DES). In addition, reaction of epoxides with thiourea in DES yields the corresponding thiiranes. Georg Thieme Verlag Stuttgart New York.
Zeolite molecular sieve 4: A reusable catalyst for fast and efficient conversion of epoxides to thiiranes with thiourea
Eisavi, Ronak,Zeynizadeh, Behzad,Baradarani, Mohammad Mehdi
experimental part, p. 1902 - 1909 (2011/10/09)
Various epoxides are readily converted to their corresponding thiiranes by thiourea/zeolite molecular sieve 4 system in refluxing MeOH. All reactions were carried out within 12-25 min to give thiiranes in 80%-99% yields. The catalyst saves its catalytic activity for several times at this transformation. Stereospecific conversion of (R)-(+)-styrene oxide to (S)-(+)-styrene episulfide was achieved by this combination system. Taylor & Francis Group, LLC.
A practical and eco-friendly method for conversion of epoxides to thiiranes with immobilized thiourea on CaCO3
Zeynizadeh, Behzad,Baradarani, Mohammad Mehdi,Eisavi, Ronak
experimental part, p. 2208 - 2215 (2012/04/04)
Solvent-free conversion of various epoxides to the corresponding thiiranes was carried out efficiently with immobilized thiourea on CaCO3. The reactions were completed within 1-12 min under oil bath (60 °C-70 °C) conditions to afford thiiranes in 88%-98% yields. Copyright Taylor & Francis Group, LLC.
Solvent-free conversion of epoxides to thiiranes by thiourea/NH4Cl system
Zeynizadeh, Behzad,Yeghaneh, Samal
experimental part, p. 2280 - 2286 (2009/08/07)
Epoxides were readily converted to the corresponding thiiranes by thiourea/NH4Cl system under solvent-free conditions. The reactions were completed within 15-75 min at 60-70°C. The thiiranes were obtained in 65-96% yields. Copyright Taylor & Francis Group, LLC.
