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Relevant academic research and scientific papers

THE INVENTION OF RADICAL REACTIONS. PART XVI. RADICAL DECARBOXYLATIVE BROMINATION AND IODINATION OF AROMATIC ACIDS

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.

How solvent modulates hydroxyl radical reactivity in hydrogen atom abstractions

The hydroxyl radical (HO) is a highly reactive oxygen-centered radical whose bimolecular rate constants for reaction with organic compounds (hydrogen atom abstraction) approach the diffusion-controlled limit in aqueous solution. The results reported herein show that hydroxyl radical is considerably less reactive in dipolar, aprotic solvents such as acetonitrile. This diminished reactivity is explained on the basis of a polarized transition state for hydrogen abstraction, in which the oxygen of the hydroxyl radical becomes highly negative and can serve as a hydrogen bond acceptor. Because acetonitrile cannot participate as a hydrogen bond donor, the transition state cannot be stabilized by hydrogen bonding, and the reaction rate is lower; the opposite is true when water is the solvent. This hypothesis explains hydroxyl radical reactivity both in solution and in the gas phase and may be the basis for a containment strategy used by Nature when hydroxyl radical is produced endogenously.

Quantum Yields in the Photochemically Induced Radical Chemistry of Acyl Derivatives of Thiohydroxamic Acids

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

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.

LIGHT INDUCED HALOGENATIVE DECARBOXYLATION OF THIOHYDROXAMIC ESTERS

The generality of lidht initiated halogenative decarboxylation of thiohydroxamic esters was studied.This method gave high yields of alkyl chlorides, bromides and iodides derived from primary, secondary and tertiairy substituted carboxylic acids.

THE INVENTION OF NEW RADICAL CHAIN REACTIONS. PART VIII. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS; A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC ACIDS.

The aliphatic and alicyclic esters of N-hydroxy-pyridine-2-thione are readily reduced by tributylstannane in a radical chain reaction to furnish nor-alkanes.In the absence of the stannane a smooth decarboxylative rearrangement occurs to give 2-substituted thiopyridines.The radicals present in this reaction provoke with t-butylthiol an efficient radical reaction with formation of nor-alkane and 2-pyridyl-t-butyl disulphide.Similarly these carbon radicals can be captured by halogen atom transfer to give noralkyl chlorides, bromides and iodides.With oxygen in the presence of t-butylthiol the corresponding noralkyl hydroperoxides are formed in another radical chain reaction.

THE FREE RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE: A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE

Optically pure (L)-vinylglycine has been synthesised by two different methods.The first of these involves protected (L)-glutamate esters of N-hydroxy-2-seleno-pyridine.Such esters are shown to undergo the same decarboxylative rearrangement as their thio-a