SN2 Reactions with Carboxylic Esters. Selective cleavage of methyl esters

✍ Scribed by Paul Müller; Bernard Siegfried

• Publisher: John Wiley and Sons
• Year: 1974
• Tongue: German
• Weight: 411 KB
• Volume: 57
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19740570404

✦ Synopsis

Abstract

Sodium cyanide in hexamethylphosphoric triamide selectively cleaves methyl esters in the presence of ethyl esters with yields of ca. 80%. The mechanism of the reaction has been investigated. It consists of nucleophilic displacement by cyanide of the carboxylate ion from the alcohol carbon atom (B~Al~2 mechanism).