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Issue 35, 2014
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Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions

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Abstract

The thioacid–azide reaction and its chemoselectivity were probed with alkyl azides for a potential application to form amide bonds in aqueous solvents. Our results reveal that under acidic conditions thioamides were formed as major reaction products suggesting a competing mechanism, whereas reactions forming amides predominated at slightly higher pH values.

Graphical abstract: Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions

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Article information


Submitted
28 Jan 2014
Accepted
12 Mar 2014
First published
12 Mar 2014

Chem. Commun., 2014,50, 4603-4606
Article type
Communication

Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions

M. Mühlberg, K. D. Siebertz, B. Schlegel, P. Schmieder and C. P. R. Hackenberger, Chem. Commun., 2014, 50, 4603
DOI: 10.1039/C4CC00774C

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