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.).
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Calo et al.
, p. 621 (1975)
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Guss,Chamberlain
, p. 1342 (1952)
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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.
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
