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Issue 21, 2013
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Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry

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Abstract

Highly strained biarylazacyclooctynone (BARAC) and analogous bioconjugation reagents were shown to undergo novel rearrangement and addition reactions leading to tetracyclic products. This may limit their practical applicability as bioorthogonal reporters for imaging biomolecules within living systems.

Graphical abstract: Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry

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Article information


Submitted
05 Apr 2013
Accepted
17 Apr 2013
First published
18 Apr 2013

Org. Biomol. Chem., 2013,11, 3436-3441
Article type
Communication

Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry

M. Chigrinova, C. S. McKay, L. B. Beaulieu, K. A. Udachin, A. M. Beauchemin and J. P. Pezacki, Org. Biomol. Chem., 2013, 11, 3436
DOI: 10.1039/C3OB40683K

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