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Literature DB >> 29707720

Origins of halogen effects in bioorthogonal sydnone cycloadditions.

Huimin Tao¹, Fang Liu, Ruxin Zeng, Zhuzhou Shao, Lufeng Zou, Yang Cao, Jennifer M Murphy, K N Houk, Yong Liang.

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.

Entities: Chemical Species

Year: 2018 PMID： 29707720 PMCID： PMC5953849 DOI： 10.1039/c8cc02128g

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

32 in total

1. Role of Orbital Interactions and Activation Strain (Distortion Energies) on Reactivities in the Normal and Inverse Electron-Demand Cycloadditions of Strained and Unstrained Cycloalkenes.

Authors: Brian J Levandowski; Trevor A Hamlin; F Matthias Bickelhaupt; K N Houk
Journal: J Org Chem Date: 2017-08-07 Impact factor: 4.354

2. Density functionals with broad applicability in chemistry.

Authors: Yan Zhao; Donald G Truhlar
Journal: Acc Chem Res Date: 2008-01-11 Impact factor: 22.384

3. Hyperconjugative, Secondary Orbital, Electrostatic, and Steric Effects on the Reactivities and Endo and Exo Stereoselectivities of Cyclopropene Diels-Alder Reactions.

Authors: Brian J Levandowski; K N Houk
Journal: J Am Chem Soc Date: 2016-12-15 Impact factor: 15.419

Origins of halogen effects in bioorthogonal sydnone cycloadditions.

1. Role of Orbital Interactions and Activation Strain (Distortion Energies) on Reactivities in the Normal and Inverse Electron-Demand Cycloadditions of Strained and Unstrained Cycloalkenes.

2. Density functionals with broad applicability in chemistry.

3. Hyperconjugative, Secondary Orbital, Electrostatic, and Steric Effects on the Reactivities and Endo and Exo Stereoselectivities of Cyclopropene Diels-Alder Reactions.

4. The activation strain model and molecular orbital theory: understanding and designing chemical reactions.

5. Halo substituent effects on intramolecular cycloadditions involving furanyl amides.

6. Computational Screening of New Orthogonal Metal-Free Dipolar Cycloadditions of Mesomeric Betaines.

Review 7. Synthesis of functionalized tetrasubstituted pyrazolyl heterocycles--a review.

8. Reactivity and regioselectivity in Diels-Alder reactions of anion encapsulated fullerenes.

9. Theory of 1,3-dipolar cycloadditions: distortion/interaction and frontier molecular orbital models.

10. Schleyer hyperconjugative aromaticity and Diels-Alder reactivity of 5-substituted cyclopentadienes.

1. Developing bioorthogonal probes to span a spectrum of reactivities.

2. Bioorthogonal Hydroamination of Push-Pull-Activated Linear Alkynes.

3. Predicting reactivity for bioorthogonal cycloadditions involving nitrones.