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Issue 40, 2018
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Origins of halogen effects in bioorthogonal sydnone cycloadditions

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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.

Graphical abstract: Origins of halogen effects in bioorthogonal sydnone cycloadditions

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Publication details

The article was received on 16 Mar 2018, accepted on 23 Apr 2018 and first published on 23 Apr 2018


Article type: Communication
DOI: 10.1039/C8CC02128G
Citation: Chem. Commun., 2018,54, 5082-5085
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    Origins of halogen effects in bioorthogonal sydnone cycloadditions

    H. Tao, F. Liu, R. Zeng, Z. Shao, L. Zou, Y. Cao, J. M. Murphy, K. N. Houk and Y. Liang, Chem. Commun., 2018, 54, 5082
    DOI: 10.1039/C8CC02128G

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