The pyridine catalysed hydrolysis of carboxylic anhydrides

✍ Scribed by C.A. Bunton; N.A. Fuller; S.G. Perry; V.J. Shiner

• Book ID: 104213319
• Publisher: Elsevier Science
• Year: 1961
• Tongue: French
• Weight: 122 KB
• Volume: 2
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71753-9

✦ Synopsis

TERTIARY amine:;, e.g. pyridine, are effective catalysts of the hydrolysis of carboxylic anhydrides. Pyridine is believed to act by converting the anhydride into an acylpyridinium ion (I). Both the formation of this ion, step 1, and its breakdown to products, step 3, have at times been postulated as the slow step of the reaction. la*!? 1 R.CO.0.CO.R t C5H5N y2 _ t RCQ.NC5H5 t RC02 II -3 Hz0 J. EC02H + CsH+l tk We have attempted to differentiate between these possibilities by studying the concurrent hydrolysis and isotopic exchange of anhydrides with '%Z-labelle d carboxylate.

In the absence of pyridine, hydrolysis of acetic anhydride in the presence of sodium acetate is accompanied by isotopic exchange between the A.R. Butler