D. Garmaise
Aug 1, 1966
Citations
0
Influential Citations
3
Citations
Journal
Canadian Journal of Chemistry
Abstract
A by-product isolated in low yield from the reaction of p-chlorobenzyl chloride with potassium thiocyanate and sodium iodide in dimethylformamide was shown to be the isotrithiocyanuric acid derivative I (R = p-chlorobenzyl). I gave the isodithiocyanuric acid ester (III) on alkaline hydrolysis, and mono-p-chlorobenzyl isotrithiocyanurate (IV) on reduction with sodium hydrosulfite. Treatment of I with sodium hypochlorite in aqueous alcoholic medium resulted in the direct replacement of the sulfhydryl group by an alkoxyl group. The N,S,S-triester VIII rearranged, on heating, to the symmetrical S,S,S-triester IX; this behavior is opposite to that shown by the oxygen analogues.