The Invention of Radical Reactions. XXXIII Homologation Reactions of Carboxylic Acids by Radical Chain Chemistry
Various carbon radicals can be generated from carboxylic acids via the corresponding Barton esters.These radicals can be used for the synthesis of longer chain homologues of the original acids.
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
p. 407 - 426
(2007/10/02)
Chain-elongation and Degradation of Carboxylic Acids by Barton-ester Based Radical Chemistry
The reaction of α-trifluoroacetoxy acrylates and acrylonitriles with carbon radicals formed from carboxylic acids gives adducts that can be transformed into vic-diols, esters, amides, and homoaldehydes in good to high yield.Aldoses can be smoothly degraded to the corresponding nor- or bis-nor compounds using radical chemistry.
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.,Shinada, Tetsuro
p. 6505 - 6508
(2007/10/02)
Homologation of carboxylic acids by improved methods based on radical chain chemistry of acyl derivatives of N-hydroxy-2-thiopyridone
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.
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
p. 5013 - 5016
(2007/10/02)
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