Sonication-induced halogenative decarboxylation of thiohydroxamic esters

Dauben, William G.; Bridon, Dominique; Kowalczyk, Bruce A.

doi:10.1021/jo00287a023

Cited by 31 publications

(9 citation statements)

References 9 publications

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“…A similar activation mechanism was proposed for a sonochemically activated reaction. 225 The Barton ester itself was shown to be stable upon sonication in benzene solutions, even in the presence of AIBN, although a rapid reaction was observed in aliphatic halogenated solvents. It was found that CCl 4 undergoes decomposition by sonication, giving chlorine and trichloromethyl radicals that initiate the reaction by addition to the Barton ester 239 .…”

Section: Pioneering and Classical Methodsmentioning

confidence: 99%

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%

Decarboxylative Halogenation of Organic Compounds

2020

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“…using mineral acids. In-situ formation of H + from halocarbons under ultrasound irradiation is well known (Scheme 3) [26][27][28][29][30].…”

Section: Dehydration Reactionsmentioning

confidence: 99%

Ultrasound in Synthetic Organic Chemistry

Schmidt¹

2005

Advances in Organic Synthesis

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“…In the first step, ultrasound irradiation promotes the formation of HCl [10][11][12][13][14][15] (see Scheme 3):…”

Section: Mechanismmentioning

confidence: 99%

“…These results could be explained by the formation of a small amount of HCl during the sonication of CHCl 3 followed by dehydration of the HMA. The formation of HX (X = Cl, Br) from halocarbons is well known [11][12][13][14][15] (see Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Dehydration reaction of hydroxenin monoacetate in carbon tetrachloride and an aliphatic alcohol under ultrasound irradiation

Aquino¹,

Bonrath²,

Schmidt³

et al. 2005

Ultrasonics Sonochemistry

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A new method for the preparation of an E/Z mixture of vitamin A acetate from hydroxenin monoacetate is described. This two-step reaction was studied by changing the reaction parameters (reaction temperature, ultrasound power, and reaction time) and the alcohol used. This approach consists of the dehydration reaction of hydroxenin monoacetate under ultrasound irradiation in CCl4 and an aliphatic alcohol under an inert atmosphere. The formation of small amounts of HCl from CCl4 and an aliphatic alcohol under ultrasound irradiation is followed by the dehydration reaction of hydroxenin monoacetate. An E/Z mixture of vitamin A acetate was obtained resulting in the desired pentaenes. Some ethers derivatives were also formed as by-products, isolated and characterized. Study of the reaction mechanism is also reported here.

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Sonication-induced halogenative decarboxylation of thiohydroxamic esters

Cited by 31 publications

References 9 publications

Decarboxylative Halogenation of Organic Compounds

Decarboxylative Halogenation of Organic Compounds

Ultrasound in Synthetic Organic Chemistry

Dehydration reaction of hydroxenin monoacetate in carbon tetrachloride and an aliphatic alcohol under ultrasound irradiation

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