NEWS

Igor Alabugin教授による大学院生向け授業が行われました。授業の詳細は以下の通りです。

Instructor: Igor Alabugin

Study Materials:

Alabugin, I. V. Stereoelectronic Effects: the Bridge between Structure and Reactivity. John Wiley & Sons Ltd, Chichester, UK, 2016. Review at https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201700616.

Alabugin, I. V.; Kuhn L. Oxygen: the Key to Stereoelectronic Control in Chemistry. ACS in Focus, 2023. https://pubs.acs.org/doi/book/10.1021/acsinfocus.7e7009.

Objectives:

This course will provide a set of tools (concepts) needed to understand molecular structure, to analyze and predict chemical reactivity in molecular and supramolecular systems. In the second part of the course, these concepts will be used to design and control a variety of cyclization and cycloaddition reactions.

Prerequisites: Good grasp of undergraduate organic and physical chemistry.

Course Outline:

1. Introduction to Chemical Bonding

From Valence-Bond Theory to variable hybridization. The Bent’s rule

1. Electronic effects – conjugation and hyperconjugation.

Conformational analysis through the stereoelectronic prism.

III. Stereoelectronic effects on reactivity.

General rules for the formation of cyclic structures

Additional Reading:

Fundamentals:

Orbital Hybridization: a Key Electronic Factor in Control of Structure and Reactivity. J. Phys. Org. Chem., 2015, 28, 147-162. http://onlinelibrary.wiley.com/doi/10.1002/poc.3382/abstract.

Hyperconjugation. WIREs: Comput. Mol. Sci. 2019, 9, e1389, https://doi.org/10.1002/wcms.1389.

Stereoelectronic effects:

Anomeric Effect, Electrostatics, and Hyperconjugation: Lessons from a Classic Stereoelectronic Phenomenon. Chem. Soc. Rev. 2021, 50, 10212-10252, https://pubs.rsc.org/en/Content/ArticleLanding/2021/CS/D1CS00564B.

Stereoelectronic Power of Oxygen in Control of Chemical Reactivity: the Anomeric Effect is not Alone. Chem. Soc. Rev. 2021, 50, 10253-10345, https://pubs.rsc.org/en/content/articlelanding/2021/cs/d1cs00386k.

Cycle-forming reactions:

The Baldwin Rules: Revised and Extended. WIREs: Comput. Mol. Sci. 2016, 6, 487–514. DOI: 10.1002/wcms.1261. http://wires.wiley.com/WileyCDA/WiresArticle/wisId-WCMS1261.html. 

Finding the right path: Baldwin “Rules for Ring Closure” and stereoelectronic control of cyclizations. Chem. Commun., 2013, 49, 11246 – 11250. http://pubs.rsc.org/en/content/articlehtml/2013/cc/c3cc43872d.

Design principles of the use of alkynes in radical cascades. Nature Reviews Chemistry, 2023, 7, 405–423, https://www.nature.com/articles/s41570-023-00479-w.

Alkyne Origami: Folding Oligoalkynes into Polyaromatics. I. V. Alabugin, E. Gonzalez-Rodriguez. Acc. Chem. Res., 2018, 51, 1206-1219. https://pubs.acs.org/doi/10.1021/acs.accounts.8b00026.