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Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition to Bicyclo[6.1.0]nonyne

preprint
revised on 24.06.2019 and posted on 24.06.2019 by Praveen Gunawardene, Wilson Luo, Alexander M. Polgar, John F. Corrigan, Mark Workentin

Highly accelerated inverse-electron-demand strain-promoted alkyne-nitrone cycloaddition (IED SPANC) between a sta- ble cyclooctyne (bicyclo[6.1.0]nonyne (BCN)) and nitrones delocalized into a Cα-pyridinium functionality is reported, with the most electron-deficient “pyridinium-nitrone” displaying among the most rapid cycloadditions to BCN that is currently reported. Density functional theory (DFT) and X-ray crystallography are explored to rationalize the effects of N- and Cα-substituent modifications at the nitrone on IED SPANC reaction kinetics and the overall rapid reactivity of pyridinium-delocalized nitrones.

History

Email Address of Submitting Author

mworkent@uwo.ca

Institution

The University of Western Ontario

Country

Canada

ORCID For Submitting Author

0000-0001-8517-6483

Declaration of Conflict of Interest

none

Version Notes

updated revised version

Exports