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