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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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Publication details

The article was received on 28 Jan 2014, accepted on 12 Mar 2014 and first published on 12 Mar 2014


Article type: Communication
DOI: 10.1039/C4CC00774C
Citation: Chem. Commun., 2014,50, 4603-4606
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    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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