関連する実験動画

Updated: Jan 8, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

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Pd-オキサゾロンの[2+2]環化付加による可視光エネルギー貯蔵

Qianfeng Qiu1, Junichi Usuba2, Wai Lean Koay3

  • 1Department of Chemistry, Brandeis University Waltham MA USA grace_han@ucsb.edu.

Chemical science
|December 22, 2025
PubMed
まとめ

新しいオルトパラジウム化オキサゾロン錯体が太陽エネルギーを捕捉・貯蔵する。これらの錯体は、可視光を利用した可逆的な[2+2]光環化付加により、効率的な分子太陽熱エネルギー貯蔵を可能にする。

キーワード:
分子太陽熱エネルギー貯蔵光環化付加パラジウム錯体オキサゾロン可視光エネルギーエネルギー貯蔵材料

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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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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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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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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