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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Original Articles

Formation of N‐Sulfonylcarbamates from Epichlorohydrin: Synthesis of Polyfunctional Oxazolidin‐2‐ones

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Pages 2215-2223 | Received 04 Oct 2006, Published online: 03 Jul 2007
 

Abstract

The addition of 3‐methylbut‐2‐enoic acid‐3‐bromo‐2‐hydroxypropyl ester 2 and 1‐bromo‐3‐phenylsulfanyl propan‐2‐ol 3, obtained from epichlorohydrin, to aroxy and alkoxysulfonyl isocyanates 1 in anhydrous ether at ambient temperature affords the corresponding N‐sulfonyl bromocarbamates 4. These are treated with triethylamine in refluxing acetone to give exclusively the corresponding polyfunctional oxazolidin‐2‐ones 5 with good yields.

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