66832-24-4Relevant articles and documents
THE INVENTION OF RADICAL REACTIONS. PART XVI. RADICAL DECARBOXYLATIVE BROMINATION AND IODINATION OF AROMATIC ACIDS
Barton, Derek H.R.,Lacher, Brigitte,Zard, Samir Z.
, p. 4321 - 4328 (1987)
Thiohydroxamic esters of aromatic carboxylic acids undergo clean decarboxylative bromination or iodination on treatment with bromotrichloromethane, iodoform or diiodomethane in the presence of a radical initiator.
Quantum Yields in the Photochemically Induced Radical Chemistry of Acyl Derivatives of Thiohydroxamic Acids
Barton, Derek H. R.,Blundell, Paul,Jaszberenyi, Joseph Cs.
, p. 6937 - 6942 (2007/10/02)
Acyl derivatives of N-hydroxyquinazoline-4-thiones are a novel source of disciplined carbon radicals.Quantum yield determination reveals that photolysis of these compounds initiates radical chains, resulting in quantum yields up to φ = 60.Comparative studies with acyl derivatives of N-hydroxy-2-thiopyridone show that the quinazoline derivatives are more light-sensitive than the thiopyridone compounds.The carbon radicals thus formed from the former can be trapped selectively, without the formation of rearranged products (i.e. without the competition of the radicophilic thiocarbonyl group of the starting material with the radical trap).
Sonication-Induced Halogenative Decarboxylation of Thiohydroxamic Esters
Dauben, William G.,Bridon, Dominique P.,Kowalczyk, Bruce A.
, p. 6101 - 6106 (2007/10/02)
The sonication of primary, secondary, and tertiary thiohydroxamic esters in CCl4 has led to their synthetic transformation to alkyl chlorides, bromides, or iodides.The high yields were comparable to the previous thermal-or photoinduced version of this same reaction.This radical reaction calls attention to the utility of ultrasound in production of trichloromethyl radical, which was concluded to initiate decomposition of the thiohydroxamic esters.
