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Reactions of phosphoric anhydride with acyclic amides. Synthesis of amidines and imides

✍ Scribed by Eva A. Oberlander; John C. Tebby


Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
140 KB
Volume
9
Category
Article
ISSN
1042-7163

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✦ Synopsis


Acyclic secondary amides such as benzanilides 1a-g, acetanilides 2a-d, and benzamide 1h undergo selfcondensation in the presence of phosphoric anhydride to produce, in one step, N-substituted aroyl benzamidines 3a-g, acyl acetamidines 4a-d, and imide 5, respectively. Mechanistic evidence is presented for nucleophilic attack by the iminol tautomers on the O-phosphorylated amides to give amidines and on the N-phosphorylated imidates to give imides.


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