Schmidt Reaction of Hydroxyalkyl Azides with Acyclic Ketones
Abstract
The Schmidt reaction of hydroxyalkyl azides with acyclic ketones has been investigated. Specifically, we show that this reaction consistently generates an ester product via hydrolysis of an intermediate iminium ether. This is in contrast to most cyclic ketones, which provide lactams. Moreover, the addition of nucleophiles to the intermediate affords amide products through a mechanistically distinct pathway. Studies related to the reaction scope, regioselectivity, and mechanism are also reported.
Fields of Study & Subjects
Advanced Synthetic Organic Chemistry
Organic and Inorganic Chemical Reactions
Chemical Reaction Mechanisms
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 8
- Pages
- 3256–3261
- Publication date
- 11 February 2026
- Language
- EN