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Hydrolysis in the absence of bulk water 1. Chemoselective hydrolysis of amides using tetrahalophthalic anhydrides

✍ Scribed by Jefferson T. Eaton; William D. Rounds; John H. Urbanowicz; Gordon W. Gribble

Book ID: 104217837
Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 252 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82395-3

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✦ Synopsis

The reaction of primary and secondary amides with tetrafluorophthalic or tetrachlorophthalic anhydride gives carboxylic acids in good yield. The reaction is chemoselective in that the amide functionality can be hydrolyzed in the presence of ester groups.

We report that the prototypical reaction between formamide (la, RI = R2 = H) and phthalic anhydride (2a, X1-4 = H), which gives formic acid (3a, RI = H) and phthalimide (4a, R2 =X14 = H) in very high yield, represents a general, efficient, and chemoselective hydrolysis of primary and secondary amides to carboxylic acids in the absence of bulk water. This transformation is summarized in the Scheme.

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Hydrolysis in the absence of bulk water

Hydrolysis in the absence of bulk water 2. Chemoselective hydrolysis of nitriles using tetrahalophthalic acids

✍ William D. Rounds; Jefferson T. Eaton; John H. Urbanowicz; Gordon W. Gribble 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 216 KB

The reaction of nitriles with tetrafluorophthalic or tetrachlorophthalic acid gives carboxylic acids in good yield. The reaction is chemoselective in that the nitrile functionality can be hydrolyzed in the presence of ester groups.