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New facile synthesis of α-hydroxyamides: Intermolecular and intramolecular catalysis in the reaction of α-hydroxycarboxylic acids with N-sulfinylamines.

✍ Scribed by Jai Moo Shin; Yong Hae Kim


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
239 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis


Sumnary: a-Hydroxycarboxylic acids (I_) reacted with N-sulfinylanilines (2) to yive the corresponding a-hydroxyanilides (2) in quantitative yields under mild condition: the reaction appears to involve intermolecular catalysis by the carboxylic acid moiety and intramolecular catalysis by the hydroxyl group.


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## Abstract Reactions of electron‐poor α‐haloketones with (__N__‐isocyanimino) triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and in neutral conditions to afford disubstituted 1,3,4‐oxadiazole derivatives in high yields. © 2010 Wiley Periodica