Origins of halogen effects in bioorthogonal sydnone cycloadditions.

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.

SUBMITTER: Tao H 

PROVIDER: S-EPMC5953849 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature