William Bolts: A Dutch Adventurer under John Companyby N. L. Hallward

Rapid amidic hydrolysis: a competitive r

Rapid amidic hydrolysis: a competitive reaction pathway under basic conditions for N-(hydroxymethyl)benzamide derivatives bearing electron-donating groups

✍ John L. Murphy; William J. Tenn III; Joseph J. Labuda; Richard W. Nagorski 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 248 KB

Studies of N-(hydroxymethyl)benzamide derivatives have concluded that the hydroxide-dependent reaction occurs via a specific-base catalyzed deprotonation of the hydroxyl group followed by ratedetermining loss of the benzamidate and generation of the aldehyde. The 3-methyl, 4-methyl, and 4-methoxy-N-