Hydrogen Sulfide Scavenging by 1,3,5-Triazinanes. Comparison of the Rates of Reaction

The reaction of 1,3,5-triethyl-1,3,5-triazinane ( 1b ) and 1,3,5-trimethyl-1,3,5-triazinane ( 1c ) with sodium hydrogen sulfide has been studied. The products were the corresponding thiadiazinanes 2 and dithiazinanes 3 . The rates of the reaction, together with that of 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane ( 1a ), were studied by 1 H NMR spectroscopy. Their relative rates of reaction with HS - were as follows: 1c, 1; 1b, 19; 1a, 31. The rates of hydrolysis were studied for the same three compounds. In this reaction, the relative rates were as follows: 1c, 1; 1b, 12; 1a, 24. The reactions of 1,3,5-trioxane ( 4a ) and 2,4,6-trimethyl-1,3,5-trioxane were also studied. These two compounds did not react with HS - or were hydrolyzed under the conditions used for the reactions of 1a − c .