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Org Biomol Chem. 2012 Apr 21;10(15):3066-70. doi: 10.1039/c2ob07165g. Epub 2012 Mar 7.

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

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1
Steacie Institute for Molecular Sciences, National Research Council Canada, 100 Sussex Drive, Ottawa, Canada.

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.

PMID:
22398581
DOI:
10.1039/c2ob07165g
[Indexed for MEDLINE]
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