LXXXIX.—The action of potassium iodide and iodate on some hydroxy-acids

Krishna, Sri; Pope, Frank George

doi:10.1039/ct9222100798

Cited by 3 publications

(3 citation statements)

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“…They subjected 4-hydroxybenzoic acid in cold sulfuric acid to bromine in an attempt to synthesize 2,6-dibromophenol, but the major isolated product from the reaction was 2,4,6-tribromophenol . Later, Krishna and Pope during their analysis of salicylic acid by the iodometric determination of acids observed significantly lower amounts of liberated iodine than expected from reaction : Evolution of carbon dioxide and iodine was observed during the reaction. However, the iodine color vanished with time, accompanied by the formation of a precipitate, which was identified as 2,4,6-triiodophenol.…”

Section: Pioneering and Classical Methodsmentioning

confidence: 99%

Section: The Hunsdiecker−borodin Reactionmentioning

confidence: 98%

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Decarboxylative Halogenation of Organic Compounds

2020

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Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for the synthesis of ubiquitous organic halides. The method is based on conversion of carboxylic acids to the corresponding organic halides via selective cleavage of a carbon–carbon bond between the skeleton of the molecule and the carboxylic group and the liberation of carbon dioxide. In this review, we discuss and analyze major approaches for the conversion of alkanoic, alkenoic, acetylenic, and (hetero)aromatic acids to the corresponding alkyl, alkenyl, alkynyl, and (hetero)aryl halides. These methods include the preparation of families of valuable organic iodides, bromides, chlorides, and fluorides. The historic and modern methods for halodecarboxylation reactions are broadly discussed, including analysis of their advantages and drawbacks. We critically address the features, reaction selectivity, substrate scopes, and limitations of the approaches. In the available cases, mechanistic details of the reactions are presented, and the generality and uniqueness of the different mechanistic pathways are highlighted. The challenges, opportunities, and future directions in the field of decarboxylative halogenation are provided.

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Section: Pioneering and Classical Methodsmentioning

confidence: 99%

Section: The Hunsdiecker−borodin Reactionmentioning

confidence: 98%

Decarboxylative Halogenation of Organic Compounds

2020

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“…Pope reported a one-step strategy for the first time [Fig. 1(A)]46. In this method, the substrate was limited to hydroxyl-substituted aromatic carboxylic acids, and no yield was reported.…”

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confidence: 99%

Simple, Efficient and Controllable Synthesis of Iodo/Di-iodoarenes via Ipsoiododecarboxylation/Consecutive Iodination Strategy

Yang

Zhang

Deng

et al. 2017

Sci Rep

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A practical, efficient, and operationally simple strategy for the ipsoiododecarboxylation and di-iodination of aromatic carboxylic acids using the low-cost commercial reagent succinimide (NIS) as iodine source is reported. This iodination or di-iodination process can be easily controlled through reaction conditions, thereby providing corresponding iodination or di-iodination products with high yields. Furthermore, these two reactions can be easily scaled up to gram-scale by using palladium catalyst (0.66 mol%), which provides high isolated yield.

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Nachweis und Bestimmung der Carboxylgruppe

Meyer

1938

Analyse Und Konstitutionsermittlung Organischer Verbindungen

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LXXXIX.—The action of potassium iodide and iodate on some hydroxy-acids

Cited by 3 publications

References 0 publications

Decarboxylative Halogenation of Organic Compounds

Decarboxylative Halogenation of Organic Compounds

Simple, Efficient and Controllable Synthesis of Iodo/Di-iodoarenes via Ipsoiododecarboxylation/Consecutive Iodination Strategy

Nachweis und Bestimmung der Carboxylgruppe

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