Lianyungang Klinechem Co.,Ltd
call us on: +86-518-88103268
English中文
Knowledge
Home > Knowledge > Content

Schmidt Reaction

Lianyungang Klinechem Co.,Ltd | Updated: Dec 17, 2018

Schmidt Reaction

The acid-catalysed reaction of hydrogen azide with electrophiles, such as carbonyl compounds, tertiary alcohols or alkenes. After a rearrangement and extrusion of N2, amines, nitriles, amides or imines are produced.


Mechanism of the Schmidt Reaction

Reaction of carboxylic acids gives acyl azides, which rearrange to isocyanates, and these may be hydrolyzed to carbamic acid or solvolysed to carbamates. Decarboxylation leads to amines.

The reaction with a ketone gives an azidohydrin intermediate, which rearranges to form an amide:

Alkenes are able to undergo addition of HN3 as with any HX reagent, and the resulting alkyl azide can rearrange to form an imine:

Tertiary alcohols give substitution by azide via a carbenium ion, and the resulting alkyl azide can rearrange to form an imine.

Recent Literature


Chemoselective Schmidt Reaction Mediated by Triflic Acid: Selective Synthesis of Nitriles from Aldehydes
B. V. Rokade, J. R. Prabhu, J. Org. Chem.201277, 5364-5370.


Efficient, One-Pot, BF3·OEt2-Mediated Synthesis of Substituted N-Aryl Lactams
D. Caturvedi, A. K. Chaturvedi, N. Mishra, V. Mishra, Synlett201223, 2627-2630.


Gold(I)-Catalyzed Intramolecular Acetylenic Schmidt Reaction
D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc.2005127, 11260-11261.


Contact Us
Address: Jingqi Road, Weiwu Road, Coastal Industrial Park, Guanyun County, Lianyungang City, Jiangsu Province
Tel:+86-518-88103268
Fax:+86-518-88103267
E-mail:sales@klinechem.com

© Lianyungang Klinechem Co.,Ltd