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Updated: May 12, 2025

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素结合促进了3,3-脱位氧化的光诱导合成

Kun-Quan Chen1, Jia Zhang2, Xiao-Bo Chen2

  • 1School of Pharmacy and Medical Technology, Putian University, Key Laboratory of Medical Microecology (Putian University), Putian 351100, China.

The Journal of organic chemistry
|April 24, 2025
PubMed
概括

一种新的光诱导,无催化剂的方法通过α-bromoanilides合成3,3-异位氧化醇. 这种激进循环依赖于光激活的电荷转移复合体,使得具有广泛基质范围的高效合成成为可能.

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the...
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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.
Selection Rules: Photochemical Activation
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