利用 9-取代基与周围位置的氯基的立体斥力实现蒽的非电子活化

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-11-01 DOI:10.1002/ajoc.202400381

Annisa Indah Reza , Kento Iwai , Nagatoshi Nishiwaki

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引用次数: 0

摘要

我们研究了在 1,8-二氯蒽框架的 9 位或 10 位引入取代基如何影响蒽环的水平和垂直变形。与 10 取代的蒽相比，9 取代的蒽显示出更大的畸变，这是由于两个氯基团在周边位置的立体排斥作用。蒽框架的畸变影响了它们的反应活性。事实上，9 取代的蒽在与马来酸酐发生 Diels-Alder 反应时表现出更高的反应活性，这是非电子活化的结果。

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Non‐Electronic Activation of Anthracenes Using Steric Repulsion of the 9‐Substituent with Chloro Groups at the peri‐Positions

We investigated how the introduction of substituent at the 9‐ or 10‐position of the 1,8‐dichloroanthracene framework affects the horizontal and vertical distortions of the anthracene rings. The 9‐substituted anthracenes showed higher distortions than their 10‐substituted counterparts due to the steric repulsion with two chloro groups at the peri‐positions. The distortion of anthracene framework affected their reactivity. Indeed, 9‐substituted anthracenes exhibited higher reactivity to undergo the Diels–Alder reaction with maleic anhydride, which was a result of non‐electronic activation.

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.