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Updated: May 2, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

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ビシナル,イミダート・ラジカル・ポラー・クロスオーバー・カスケードによるアルコールの二重C-H機能化

Allen F Prusinowski1, Raymond K Twumasi1, Ethan A Wappes1

  • 1Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.

Journal of the American Chemical Society
|March 7, 2020
PubMed
まとめ

この研究は,アリファティックアルコールにおける近隣 sp3 C-H 結合の二重機能化のための新しい方法を導入している. このプロセスでは,ベータアミンとガンマヨジドを1つのステップで効率的に組み込み,ラジカル-極性クロスオーバーカスケードを使用します.

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Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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