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Issue 15, 2012
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Kinetics studies of rapid strain-promoted [3 + 2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone

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Abstract

Strain-promoted cycloadditions of cyclic nitrones with biaryl-aza-cyclooctynone (BARAC) proceed with rate constants up to 47.3 M−1 s−1, this corresponds to a 47-fold rate enhancement relative to reaction of BARAC with benzyl azide and a 14-fold enhancement over previously reported strain promoted alkyne–nitrone cycloadditions (SPANC). Studies of the SPANC reaction using the linear free energy relationship defined by the Hammett equation demonstrated that the cycloaddition reaction has a rho value of 0.25 ± 0.04, indicating that reaction is not sensitive to substituents and thus should have broad applicability.

Graphical abstract: Kinetics studies of rapid strain-promoted [3 + 2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone

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Publication details

The article was received on 22 Dec 2011, accepted on 07 Feb 2012 and first published on 09 Feb 2012


Article type: Paper
DOI: 10.1039/C2OB07165G
Citation: Org. Biomol. Chem., 2012,10, 3066-3070
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    Kinetics studies of rapid strain-promoted [3 + 2]-cycloadditions of nitrones with biaryl-aza-cyclooctynone

    C. S. McKay, M. Chigrinova, J. A. Blake and J. P. Pezacki, Org. Biomol. Chem., 2012, 10, 3066
    DOI: 10.1039/C2OB07165G

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