17066-32-9Relevant academic research and scientific papers
Regio- and Stereoselective Synthesis of Dithiocarbonates under Ambient and Solvent-Free Conditions
Diebler, Johannes,Spannenberg, Anke,Werner, Thomas
, p. 2027 - 2030 (2016/07/07)
Herein, we report on the utilization of readily available lithium tert-butoxide as an efficient catalyst for the addition of carbon disulfide to terminal and internal epoxides under ambient conditions. Notably, the reaction proceeds regio- and stereoselectively. By applying the optimized conditions, 14 terminal and internal epoxides were converted. The desired cyclic dithiocarbonates were isolated in yields up to 95 % after simple filtration over silica. NMR spectroscopy experiments to identify the mode of activation were performed, and they indicated activation of carbon disulfide by the catalyst. The reaction of cis-2,3-butyleneoxide gave only the trans-dithiocarbonate, whereas the conversion of (R)-propylen oxide gave the respective thiocarbonate stereoselectively as one enantiomer (>99 % ee) in 87 % yield.
Isolation of the key intermediates in the catalyst-free conversion of oxiranes to thiiranes in water at ambient temperature
Kleiner, Christian M.,Horst, Luise,Wuertele, Christian,Wende, Raffael,Schreiner, Peter R.
supporting information; experimental part, p. 1397 - 1403 (2009/12/04)
Herein we shed light on the mechanism of the reaction of epoxides with ammonium thiocyanate to give the corresponding thiiranes in water, and we present a computational mechanistic model for this highly useful reaction.
