1498-99-3Relevant articles and documents
Ring enlargement and sulfur-transfer processes in SiO2-catalyzed reactions of thiocarbonyl compounds with optically active oxiranes
Malaschichin, Sergej,Fu, Changchun,Linden, Anthony,Heimgartner, Heinz
, p. 3253 - 3262 (2005)
The reactions of 1,3-dioxolane-2-thione (3) with (S)-2-methyloxirane ((S)-1) and with (R)-2-phenyloxirane ((R)-2) in the presence of SiO2 in anhydrous dichloroalkanes led to the optically active spirocyclic 1,3-oxathiolanes 8 with Me at C(7) and 9 with Ph at C(8), respectively (Schemes 2 and 3). The analogous reaction of 1,3-dimethylimidazolidine-2-thione (4a) with (R)-2 yielded stereoselectively (S)-2-phenylthiirane ((S)-10) in 83% yield and 97% ee together with 1,3-dimethylimidazolidin-2-one (11a). In the cases of 3-phenyloxazolidine-2-thione (4b) and 3-phenylthiazolidine-2-thione (4c), the reaction with (RS)-2 yielded the racemic thiirane (RS)-10, and the corresponding carbonyl compounds 11b and 11c (Scheme 4 and Table 1). The analogous reaction of 4a with 1,2-epoxycyclohexane (=7-oxabicyclo[4.1.0]heptane; 7) afforded thiirane 12 and the corresponding carbonyl compound 11a (Scheme 5). On the other hand, the BF3-catalyzed reaction of imidazolidine-2-thione (5) with (RS)-2 yielded the imidazolidine-2-thione derivative 13 almost quantitatively (Scheme 6). In a refluxing xylene solution, 1,3-diacetylimidazolidine-2-thione (6) and (RS)-2 reacted to give two imidazolidine-2-thione derivatives, 13 and 14 (Scheme 7). The structures of 13 and 14 were established by X-ray crystallography (Fig.).
Dichloro (5,10,15,20-tetraphenylporphyrin) phosphorus(V) chloride as a new catalyst for conversion of 1,2-epoxyethanes to 2-hydroxyethyl thiocyanates with ammonium thiocyanate
Sharghi, Hashem,Nejad, Alireza Hassani
, p. 2297 - 2305 (2004)
A convenient and efficient procedure for the cleavage of the oxirane rings with ammonium thiocyanate in the presence of phosphorus(V)tetraphenylporphyrin is described. The ring-opening of 1,2-epoxyethanes is found to proceed regioselectively under mild reaction conditions. Thus, several 2-hydroxyethyl thiocyanates, useful intermediates toward biologically active molecules, are easily obtained in very good yields.
Metalloporphyrins as new catalysts in the mild, efficient and regioselective conversion of epoxides to β-hydroxy thiocyanates with NH4SCN
Sharghi, Hashem,Nejad, Alireza Hassani,Nasseri, Mohammad Ali
, p. 946 - 951 (2004)
The regioselective cleavage of 1,2-epoxyethanes to 2-hydroxyethyl thiocyanates with ammonium thiocyanates in the presence of some metalloporphyrins has been studied. The epoxides were subject to cleavage by NH4SCN in the presence of these catal
ZnFe2O4 nanoparticles: A green and recyclable magnetic catalyst for fast and regioselective conversion of epoxides to vicinal hydroxythiocyanates using NH4SCN under solvent-free conditions
Eisavi, Ronak,Alifam, Somayieh
, p. 211 - 217 (2017/11/10)
ZnFe2O4 nanoparticles were synthesized and used as recyclable magnetic catalyst in the solvent-free conversion of different epoxides to vicinal hydroxythiocyanates with NH4SCN at room temperature. The reactions were carrie
A Highly Regioselective Palladium-Catalyzed O,S Rearrangement of Cyclic Thiocarbonates
Mahy, William,Cabezas-Hayes, Sinéad,Kociok-K?hn, Gabriele,Frost, Christopher G.
, p. 6441 - 6444 (2017/11/13)
This work describes an operationally simple catalytic synthesis of cyclic S-thiocarbonates with predictable regioselectivity in good yields. The reaction utilizes substrates derived from ubiquitous 1,2-diols in an atom economical intramolecular rearrangement, catalysed by an inexpensive and simple catalyst–ligand system. A crystal structure is presented that clearly confirms the regioselectivity of the reaction.
Green synthesis of thiiranes from oxiranes under solvent- and catalyst-free conditions
Akhlaghinia, Batool,Rahimizadeh, Mohammad,Eshghi, Hosein,Zhaleh, Sara,Rezazadeh, Soodabeh
experimental part, p. 351 - 361 (2012/08/27)
A simple and efficient method for the conversion of oxiranes to thiiranes using ammonium thiocyanate (NH4SCN) under solvent- and catalyst-free conditions is described. These conditions enable clean and fast conversion of oxiranes to the corresponding thiirane.
Fast, efficient and regioselective conversion of epoxides to β-hydroxy thiocyanates with NH4SCN/zeolite molecular sieve 4 A under solvent-free conditions
Eisavi, Ronak,Zeynizadeh, Behzad,Baradarani, Mohammad Mehdi
scheme or table, p. 630 - 634 (2011/12/03)
Solvent-free conversion of various epoxides to their corresponding β-hydroxy thiocyanates was carried out successfully with NH 4SCN/zeolite molecular sieve 4 A system at room temperature. The reactions were completed within 2 - 7 min to give th
Reaction between epoxides and carbon disulfide under hydrotalcite catalysis: Eco compatible synthesis of cyclic dithiocarbonates
Maggi, Raimondo,Malmassari, Clara,Oro, Chiara,Pela, Roberto,Sartori, Giovanni,Soldi, Laura
, p. 53 - 56 (2008/09/20)
Cyclic dithiocarbonates were prepared in good yield and excellent selectivity through an environmental acceptable methodology involving the reaction of substituted epoxides with carbon disulfide under hydrotalcite catalysis. The catalyst can be recovered by filtration and reused several times. Georg Thieme Verlag Stuttgart.
A facile and efficient one-pot synthesis of thiirans by the reaction of benzoxazolyl β-ketosulfides with NaBH4/NaOH
Yamada, Nobuhiko,Mizuochi, Masayoshi,Takeda, Masahiro,Kawaguchi, Hiroyuki,Morita, Hiroyuki
, p. 1166 - 1168 (2008/09/18)
Convenient and efficient procedures for thiirans have been developed via a one-pot reaction of benzoxazolyl β-ketosulfides with NaBH4 and NaOH in MeOH and THF. The reaction is considered to proceed via the spiro intermediate by the ipso-additio
Thermolysis of β-hydroxysulfides bearing several heteroaromatics
Yamada, Nobuhiko,Mizuochi, Masayoshi,Morita, Hiroyuki
, p. 3408 - 3414 (2007/10/03)
Thermolyses of β-hydroxysulfides 2, bearing groups, such as 2-benzothiazolyl and 4-(4-methyl)-4H-1,2,4-triazolyl groups, were studied and found to afford the corresponding substituted styrenes 5 and hydroxy heteroaromatics in good yields, respectively. The product distribution change in the course of the thermolysis of 2a was also studied. The olefin products 5a were considered to be formed by the thermal desulfurization of the corresponding thiiranes 4a initially formed via the five-membered spiro intermediate 6a.
