77541-96-9Relevant academic research and scientific papers
Efficient synthesis of 1,2,4-dithiazolidine-3,5-diones [dithiasuccinoyl- amines] from bis(chlorocarbonyl)disulfane plus bis(trimethylsilyl)amines
Barany, Michael J.,Hammer, Robert P.,Merrifield,Barany, George
, p. 508 - 509 (2007/10/03)
The 1,2,4-dithiazolidine-3,5-dione heterocycle, also referred to as a dithiasuccinoyl (Dts)-amine, serves as a readily removable amino protecting group for building blocks used in syntheses of peptides, glycopeptides, and PNA; it is also useful as a masked isocyanate and (inversely) as a sulfurization reagent for trivalent phosphorus. Bis(chlorocarbonyl)disulfane, the two-sulfur analogue of succinyl chloride, has been envisioned as a reagent for facile single-step elaboration of the heterocycle. However, reactions of bis(chlorocarbonyl)disulfane directly with primary amines fail to yield Dts-amines for reasons that are discussed. Inspired by several precedents from the organosilicon chemistry literature that a trimethylsilyl group may serve as a "large proton," a successful, high-yield preparation of Dts-amines through reactions of bis(chlorocarbonyl)disulfane with bis(trimethylsilyl)amines has been developed. Studies aimed at elucidating mechanistic reasons for these observations are also presented. Copyright
SULFENYL CHLORIDES, XII. BIS-TRICHLOROMETHANESULFENYLATED DITHIOCARBAMATES
Stajer, G.,Reisch, J.,Szabo, A. E.
, p. 99 - 104 (2007/10/02)
Mono- and bis-trichloromethanesulfenylated derivatives of aryl dithiocarbamates have been prepared.It has been found that the resulting trithiopercarbamates are unstable, and are converted in air by desulfuration into carbamates, particularly during chromatographic purification.The structure of the iminomethane derivatives obtained by sulfenylation has been verified by IR and 13C-NMR spectroscopy.
