Sodium Sulfide in the Synthesis of N-Alkyl-1,3,5-dithiazinanes and 1,3,5-Thiadiazinanes.

An approach to the synthesis of 1,3,5-dithiazinanes and 1,3,5-thiadiazinanes was developed based on the cyclothiomethylation of aliphatic amines with 9-aqueous Na2S and CH2O. Linear aliphatic primary amines form predominantly 1,3,5-thiadiazinanes, while branched ones lead to the formation of 1,3,5-dithiazinanes. [ABSTRACT FROM AUTHOR]