The Degradation Of Carboxylic Acid Salts By Means Of Halogen - The Hunsdiecker Reaction

Johnson, Robert G.; Ingham, Robert K.

doi:10.1021/cr50008a002

Cited by 233 publications

(85 citation statements)

References 80 publications

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“…A series of related radical halodecarboxylatios transformations are known: the Hunsdiecker-Borodine [93][94][95] and the Simonini reaction [96]. These transformations convert carboxylate salts into the corresponding alkyl and aryl halides in the presence of oxidizing Br 2 and I 2 respectively.…”

Section: Barton Mccombie Decarboxylation and Electrochemical Variant mentioning

confidence: 99%

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

Luca

Fenwick

2015

Journal of Photochemistry and Photobiology B: Biology

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Available online xxxx a b s t r a c tThe present review covers organic transformations involved in the reduction of CO 2 to chemical fuels. In particular, we focus on reactions of CO 2 with organic molecules to yield carboxylic acid derivatives as a first step in CO 2 reduction reaction sequences. These biomimetic initial steps create opportunities for tandem electrochemical/chemical reductions. We draw parallels between long-standing knowledge of CO 2 reactivity from organic chemistry, organocatalysis, surface science and electrocatalysis. We point out some possible non-faradaic chemical reactions that may contribute to product distributions in the production of solar fuels from CO 2 . These reactions may be accelerated by thermal effects such as resistive heating and illumination.

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Section: Barton Mccombie Decarboxylation and Electrochemical Variant mentioning

confidence: 99%

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

Luca

Fenwick

2015

Journal of Photochemistry and Photobiology B: Biology

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“…or reagents; after 1 h the solutions were analyzed for the extent of benzoyl hypochlorite decomposition and for chlorobenzene formation (Tables 1-4). 5 From an examination of these Tables, the following points may be noted. First, light (at all temperatures) and AIBN (at 60") accelerated the decomposition of the acyl hypochlorite, as would be expected since the reaction is known to be a free radical chain process (4,5).…”

Section: Resultsmentioning

confidence: 99%

“…The reactions compared included the decomposition to chlorobenzene and CO,, addition t o olefins, electrophilic chlorination of arenes, and free radical halogenation of alkanes. The reaction between halogens and silver carboxylates is the basis of the Hunsdiecker halodecarboxylation reaction (4,5), which has been supposed t o involve an acyl hypohalite as an intermediate. It was proposed therefore that the reaction of chloride ion with benzoyl peroxide also gives rise 'Presented in part at the 160th National Meeting of the American Chemical Society, Chicago, Illinois, September 1970 -.…”

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The Decomposition of Benzoyl Hypochlorite in the Presence of Metal Ions

Bunce¹,

Urban²

1971

Can. J. Chem.

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The decomposition of benzoyl hypochlorite, the intermediate in the Hunsdiecker reaction between chlorine and silver benzoate, is accelerated by light and by azobisisobutyronitrile (AIBN), but not by transition metal ions. The molar yield of the chlorobenzene produced in the decomposition increases as the temperature of the reaction mixture is raised, but is independent of whether or not the reaction is promoted by light or AIBN. It is suggested that this variation in the yield is a result of the readier decarboxylation at higher temperatures of the benzoyloxy radicals which are believed to be intermediates in the decomposition process. No such pronounced effect of temperature on the yield of halides from aliphatic silver carboxylates has been observed, presumably because aliphatic acyloxy radicals decarboxylate readily even at low temperatures.

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“…The molecular formula is C 11 H 22 O 2 . The acid G has one more C than the alcohol H because it is degraded by one C in the Hunsdiecker reaction [7,8] …”

Section: Solutionmentioning

confidence: 99%

Designing Exercises to Determine the Structural Formula of Organic Compounds Based on the Experimental Data

Giac¹,

Thanh²,

Ninh³

et al. 2017

WJCE

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This paper introduces the way to design exercises to determine the structural formula of organic compounds based on the experimental data. They are structure, physical properties, typical chemical properties, synthesis methods and application. From that the authors have built the scheme to design exercises. On that basis, the authors compiled some exercises which are used for teaching and learning organic chemistry in university and high school.

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The Degradation Of Carboxylic Acid Salts By Means Of Halogen - The Hunsdiecker Reaction

Cited by 233 publications

References 80 publications

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

The Decomposition of Benzoyl Hypochlorite in the Presence of Metal Ions

Designing Exercises to Determine the Structural Formula of Organic Compounds Based on the Experimental Data

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