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Updated: Aug 24, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Published on: April 22, 2016

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非対称な光化学 [2 + 2] - アサイクリックビニルピリジンのサイクロアディション テルナー複合体の形成と制御されない感受性メカニズム

Zebediah C Girvin1, Laura F Cotter1, Hyung Yoon1

  • 1Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut06511, United States.

Journal of the American Chemical Society
|October 20, 2022
PubMed
まとめ

三重エネルギー伝送の光化学反応でステレオ化学的制御を達成することは困難です. この研究では,イリジウム光触媒を使用して,組織化された移行状態を通じて [2 + 2]光サイクル添加において高い選択性を達成するための新しい戦略を提示しています.

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Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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