Isolation of the key intermediates in the catalyst-free conversion of oxiranes to thiiranes in water at ambient temperature.
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.
Kleiner
Christian M
CM
Justus-Liebig-Universität, Institut für Organische Chemie, Heinrich-Buff-Ring 58, 35392, Giessen, Germany.
Horst
Luise
L
Würtele
Christian
C
Wende
Raffael
R
Schreiner
Peter R
PR
D002384:Catalysis; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D005027:Ethylene Oxide / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature; D013861:Thiocyanates / Q000737:chemistry; D014867:Water / Q000737:chemistry*
D013440:Sulfides; D013861:Thiocyanates; D014867:Water; C013523:ethylene sulfide; C026976:thiocyanic acid; D005027:Ethylene Oxide