2420-60-2Relevant articles and documents
Degradation in Aqueous Solution of O-Aryl N-Arylthioncarbamates to Aryloxide Ions and Isothiocyanates. A Study of Leffler's Assumption
Hill, Stephen V.,Thea, Sergio,Williams, Andrew
, p. 437 - 446 (1983)
Rate constants for the title reaction have been measured in both forward and reverse directions leading to rates and equilibrium constants for all steps in equation (i).The effects of varying the structures of Ar and Ar' on the equilibrium and rate constants were measured; identical Leffler-Grunwald indices (α=βF/βEQ=d log k/d log K) for the addition step are observed for variation in Ar and Ar' although individual β values are markedly different.Identical α parameters arising from different substituent interaction pathways to a single bond are required if the reaction conforms to the Leffler assumption; on this basis the α parameter is considered a good measure of transition-state structure relative to reactant- and product-states for the addition reaction. 'Effective charges' on the phenolic oxygen in the thioncarbamate and its conjugate base indicate considerable C(1+)-S(1-) character in the formal thioncarbamoyl bond.
Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process
Li, Zheng-Yi,Ma, Hong-Zhao,Han, Chen,Xi, Hai-Tao,Meng, Qi,Chen, Xin,Sun, Xiao-Qiang
, p. 1667 - 1674 (2013/07/19)
A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates. Georg Thieme Verlag Stuttgart, New York.