Unusual reactivity of N-acyl imides: N-aroyl-1,2,4-dithiazolidine-3,5-diones as acyl isocyanate equivalents.
نویسندگان
چکیده
Crystalline samples of three N-aroyl-1,2,4-dithiazolidine-3,5-diones have been prepared as the first examples of a novel class of compound that displays the reactivity of an acyl isocyanate when treated with nucleophiles.
منابع مشابه
Unexpectedly Stable (Chlorocarbonyl)(N-ethoxycarbonylcarbamoyl)disulfane, and Related Compounds That Model the Zumach-Weiss-Kühle (ZWK) Reaction for Synthesis of 1,2,4-Dithiazolidine-3,5-diones.
The Zumach-Weiss-Kühle (ZWK) reaction provides 1,2,4-dithiazolidine-3,5-diones [dithiasuccinoyl (Dts)-amines] by the rapid reaction of O-ethyl thiocarbamates plus (chlorocarbonyl)sulfenyl chloride, with ethyl chloride and hydrogen chloride being formed as coproducts, and carbamoyl chlorides or isocyanates generated as yield-diminishing byproducts. However, when the ZWK reaction is applied with ...
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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 suc...
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 6 22 شماره
صفحات -
تاریخ انتشار 2008