New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water

A simple and efficient one-pot synthesis was developed for the preparation of S -alkyl thiolcarbamates from xanthogenate without catalyst using water as a solvent. The water can be recycled after removal of the product. The significant features of this protocol are: operational simplicity, mild reac...

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Bibliographic Details
Published in:Monatshefte für Chemie 2013-12, Vol.144 (12), p.1833-1837
Main Authors: Milosavljević, Milutin M., Mijin, Dušan Ž., Milisavljević, Smiljka S., Elezović, Nataša M., Milanović, Jelena K.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Summary:A simple and efficient one-pot synthesis was developed for the preparation of S -alkyl thiolcarbamates from xanthogenate without catalyst using water as a solvent. The water can be recycled after removal of the product. The significant features of this protocol are: operational simplicity, mild reaction conditions, recycling of solvent and high product yields. Starting basic alkyl xanthogenate reacts with alkyl ammonium sulfate (aryl ammonium sulfate) and hydrogen peroxide (molar ratio 1:0.55:1) in water at 40 °C for 1 h, followed by additional heating at 70–110 °C for 1–2.3 h. Good to excellent yields were achieved using ammonium sulfate in 10 % molar excess. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-013-1083-7