Reactions of S-alkyl-NN-disubstituted thioamide salts. Part 3. Thiocarbamoyl cyanide derivatives

Abstract

Two tetrahedrally substituted thiocarbamoyl cyanide derivatives have been found to undergo rearrangement on heating with morpholine. Bis(methylthio)-4-morpholinoacetonitrile (7) and methylthio-4-morpholinomalononitrile (8) were synthesised from SS′-dimethyl-N-(3-oxapentamethylene)dithiocarbamidium iodide (4), and, with morpholine gave tris-(3-oxapentamethylene)guanidinium thiocyanate (5; X = SCN) and reduction componds. The salt (4) also reacted with morpholine to give the guanidinium iodide (5; X = I) and with hydrogen sulphide giving dimethyl trithiocarbonate.