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Origins of halogen effects in bioorthogonal sydnone cycloadditions

Published Web Location

https://doi.org/10.1039/c8cc02128g
Abstract

Halogen substituents increase sydnone cycloaddition reactivities substantially. Fluoro-sydnones are superior to bromo- and chloro-sydnones, and can achieve extremely high second-order rate constants with strained alkynes. Computational studies have revealed the fluorine substituent increases the reactivity of sydnone mainly by lowering its distortion energy.

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