Collect. Czech. Chem. Commun. 1997, 62, 1491-1496

A Convenient One-Pot Synthesis of α-Isothiocyanatoethers and Unusual Course of Some of Its Nucleophilic Displacement Reactions

Juraj Bernát, Pavol Kristian, Jana Guspanová, Ján Imrich and Tatiana Bušová

Department of Organic Chemistry, P. J. Šafárik University, 041 67 Košice, Slovak Republic


A simple new method has been devised for the preparation of α-isothiocyanatoethers 1a-1f in good yields by reaction of PO(NCS)3 or (PhO)2PONCS with an equimolar mixture of aldehydes and alcohols. The course of nucleophilic additions of methanol, amines and hydrazine to 1a-1f is described.

Keywords: Isothiocyanates; Thiocarbamates; Thioureas; Thiosemicarbazides.