Thiophosgene

Synthesis of Isothiocyanates and Unsymmetrical Thioureas with the Bench-Stable Solid Reagent (Me4N)SCF3

“…This includes ortho-keto (2), -nitrile (9), and -methoxy (10) functionalities and even the bulky tert-butyl group (7). Additional valuable functional groups, such as nitro (5), thioether (8), halogens (11), ester (16 and 19), and tertiary amine (15), were also shown to be well tolerated, and electron-deficient amines that otherwise react sluggishly by established methods proved to be efficiently transformed also. Moreover, the heterocyclic isothiocyanates (12 and 13) could be synthesized in high yields (75% to 99%).…”

“…Applications range from synthetic intermediates en route to heterocycles, to food additives and compounds of medicinal importance . Synthetic access to isothiocyanates is realized primarily through the reaction of primary amines with a highly electrophilic “CS” source, such as carbon disulfide, thiophosgene, , or related thiocarbonyl transfer agents (see Figure ), e.g. thiocarbonyl­diimidazole and dipyridyl­thiono­carbonate (DPT) .…”