Elsevier

Tetrahedron Letters

Volume 33, Issue 35, 25 August 1992, Pages 5013-5016
Tetrahedron Letters

Homologation of carboxylic acids by improved methods based on radical chain chemistry of acyl derivatives of N-hydroxy-2-thiopyridone

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Abstract

Reaction of substituted terminal olefins with carbon radicals generated carboxylic acids gives adducts that can be transformed to one carbon atom longer homo-acids in high overall yield. With 6b yields are very good and the conditions of hydrolysis exceptionally mild.

Carboxylic acids (1) were transformed to their Cn+1 (6) homologues in good to high yielding reactions involving carbon radicals (3) generated from the corresponding Barton esters (2).

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