Volume 24, Issue 14
Preparative Organic Chemistry
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ChemInform Abstract: Aryl Radical Cyclizations Involving an Amide Group in the Linking Chain.

K. JONES

K. JONES

Dep. Chem., King′s Coll. London, Strand, London WC2R 2LS, UK

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J. M. D. STOREY

J. M. D. STOREY

Dep. Chem., King′s Coll. London, Strand, London WC2R 2LS, UK

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First published: April 6, 1993

Abstract

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ChemInform Abstract

Cyclization of the aryl radicals derived from the N-allyl-N-o- bromophenylacrylamides (I) or (III) proceeds under exclusive attack at the acryloyl double bond to offer a useful method for the synthesis of the N-allyloxindoles (II) or (IV). In contrast, conformational contraints around the aryl C-N bond of the radical derived from (VI) enable a novel radical translocation reaction leading to the formation of the N-phenylpyrrolidinone (VII).

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