The tandem intermolecular Paternò–Büchi reaction: Formation of tetrahydrooxepins

CY Gan, JN Lambert

Index: Gan, Chee Yong; Lambert, John N. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 15 p. 2363 - 2372

Full Text: HTML

Citation Number: 8

Abstract

The Paternò–Büchi reaction is the [2+ 2] photocycloaddition between carbonyl compounds and electron rich alkenes to generate oxetane products. By the introduction of substituted cyclopropyl rings to the alkene components, the utility of this reaction has been extended to facilitate the synthesis of substituted tetrahydrooxepins. It is proposed that initial addition of oxygen radicals to cyclopropyl enol ethers generates cyclopropylmethyl radicals which, ...

Related Articles:

Aryl-Substituted Cyclopropyl Acetylenes as Sensitive Mechanistic Probes in the Gold-Catalyzed Hydration of Alkynes. Comparison to the Ag (I)-, Hg (II)-, and Fe (III)- …

[Velegraki, Georgia; Stratakis, Manolis Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8880 - 8884]

Stereoselective Preparation of Cyclopropylmagnesium Reagents via a Br-Mg Exchange Using i-PrMgCl× LiCl in the Presence of Dioxane

[Rauhut, Christian B.; Cervino, Christian; Krasovskiy, Arkady; Knochel, Paul Synlett, 2009 , # 1 p. 67 - 70]

Copper-catalyzed electrosynthesis of 1-acyl-2, 2-diphenylcyclopropanes and their behaviour in acidic medium

[Oudeyer, Sylvain; Leonel, Eric; Paugam, Jean Paul; Nedelec, Jean-Yves Tetrahedron, 2003 , vol. 59, # 7 p. 1073 - 1081]

Aryl-Substituted Cyclopropyl Acetylenes as Sensitive Mechanistic Probes in the Gold-Catalyzed Hydration of Alkynes. Comparison to the Ag (I)-, Hg (II)-, and Fe (III)- …

[Velegraki, Georgia; Stratakis, Manolis Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8880 - 8884]

Aryl-Substituted Cyclopropyl Acetylenes as Sensitive Mechanistic Probes in the Gold-Catalyzed Hydration of Alkynes. Comparison to the Ag (I)-, Hg (II)-, and Fe (III)- …

[Velegraki, Georgia; Stratakis, Manolis Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8880 - 8884]

More Articles...