145144-82-7Relevant academic research and scientific papers
Two carbon homologation of carboxylic acids using acrylamide as a radical trap
Barton, Derek H.R.,Liu, Wansheng
, p. 2431 - 2434 (1997)
Photolysis of O-acyl derivatives of N-hydroxy-2-thiopyridone in the presence of acrylamide in dichloromethane furnished crystalline 2-(pyridine-2-thiyl)-carboxamides. Desulfurization of the latter by nickel boride afforded primary amides in excellent yields.
A convenient and general tin-free procedure for radical conjugate addition
Ollivier, Cyril,Renaud, Philippe
, p. 925 - 928 (2007/10/03)
An environmentally friendly one-pot reaction for conjugate radical additions to activated olefins, with good to excellent yields, uses organoboranes generated in situ as radical precursors and the Barton carbonate PTOC-OMe as a radical-chain transfer reag
The invention of radical reactions. Part XXXVIII. Homologation of carboxylic acids with acrylamide and synthetic studies of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and its 4-epimer
Barton, Derek H. R.,Liu, Wansheng
, p. 12067 - 12088 (2007/10/03)
Alkyl radicals generated from O-acyl derivatives of N-hydroxy-2-thiopyridone added onto acrylamide at room temperature to form crystalline 2-(2-pyridylsulfanyl)-carbosamides. Desulfurization of the latter by nickel boride at roam temperature afforded primary amides in quantitative yield. 3-Deoxy-D-arabino-2-heptulosonic acid (DAH), its 4-epimer, and their derivatives were effectively synthesized from commercial D-ribonolactone by similar radical chemistry.
The invention of radical reactions. Part XXXIV. Homologation of carboxylic acids to α-keto carboxylic acids by Barton-ester based radical chain chemistry
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
, p. 1867 - 1886 (2007/10/02)
Carboxylic acids can be transformed into the homologous α-keto acids by Barton-ester based radical chemistry. The method was especially successful when ethyl α-trifluoroacetoxy acrylate was used as a radical trap.
Two Carbon Homologation of Carboxylic Acids via Carbon Radicals Generated from the Acyl Derivatives of N-Hydroxy-2-thiopyridone: Synthesis of Cn+2 α-Keto-acids from Cn Acids. (The 'Three carbon' Problem).
Barton, Derek H. R.,Chern, Ching-Yuh,Jaszberenyi, Joseph Cs.
, p. 5017 - 5020 (2007/10/02)
Reaction of olefins containing a three carbon atom chain with carbon radicals generated from carboxylic acids furnishes adducts that are precursors of the corresponding two carbon atom longer α-keto-acids.These keto-acids are furnished in high overall yield.
