Volume 31, Issue 23
Preparative Organic Chemistry
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ChemInform Abstract: Replacing Tin in Radical Chemistry: N-Ethylpiperidine Hypophosphite in Cyclization Reactions of Aryl Radicals.

Concepcion Gonzalez Martin

Concepcion Gonzalez Martin

Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK

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John A. Murphy

John A. Murphy

Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK

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Christopher R. Smith

Christopher R. Smith

Dep. Pure Appl. Chem., Univ. Strathclyde, Glasgow G1 1XL, UK

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First published: 08 June 2010

Abstract

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ChemInform Abstract

The use of N-ethylpiperidine hypophosphite (EPHP) in radical cyclization reactions shows that the reagent has some advantages over tributyltin hydride. Thus, the cyclization proceeds well and with respectable yields, even when the substrates present terminal alkenes. Furthermore, the phosphorus-centered radicals show higher chemoselectivity over tributyltin radicals (syringe-pump addition of EPHP can improve the yields).

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