Fluorocarbon Chemistry. IV. The Preparation and Some Reactions of Silver Undecafluorocyclohexanecarboxylate

Brice, T. J.; Simons, J. H.

doi:10.1021/ja01152a507

Cited by 11 publications

(6 citation statements)

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“…Carbon disulfide has been reported to be more satisfactory than carbon tetrachloride when mercury salts are used (101). Perfluorinated hydrocarbons (54,171), amines (35,54,171), and ethers (54, 171) have found use in the preparation of perfluoroalkyl halides, but often these compounds are prepared in the absence of solvent (81,82,83,87,171).…”

Section: Materials and Methods3mentioning

confidence: 99%

“…Similarly, heptafluoro-4-iodo-l-butene has been prepared from heptafluoro-4-butenoic acid HCBr HCCOOAg With the monoesters of aliphatic dicarboxylic acids, good yields of -haloesters are obtained (4,15,21,96,97,99,100,101,102,104,120,176). Although silver succinate gives only [32][33][34][35][36][37] per cent yields of 1,2-dibromoethane (50), the silver salt of the monoethyl ester of succinic acid gives a 65 per cent yield of ethylbromopropionate (15).…”

Section: Cooagmentioning

confidence: 99%

“…Silver undecafluorocyclohexanecarboxylate has been converted to the monoiodo and monobromo cyclic fluorocarbons in good yield (35,171). Details of the preparation of the corresponding chloro compound (72) have not been published.…”

Section: Cd3cooag Cd3brmentioning

confidence: 99%

See 2 more Smart Citations

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

Johnson¹,

Ingham²

1956

Chem. Rev.

238

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Section: Materials and Methods3mentioning

confidence: 99%

Section: Cooagmentioning

confidence: 99%

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

Johnson¹,

Ingham²

1956

Chem. Rev.

238

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“…[266] Cyclizations and cycloadditions of fluorinated intermediates. The Dieckmann condensation of gem-difluorinated diester 352 was the earliest approach to 4,4-difluorocyclohexanone (300) reported by Roberts and co-workers in 1968 (Scheme 98). [267] Early synthesis of 1,1-difluoro-3-phenylcyclobutane (355) relied on [2 + 2] cycloaddition of styrene and 1,1-dichloro-2,2difluoroethylene (Scheme 99).…”

Section: Other Gem-difluorocycloalkyl Building Blocksmentioning

confidence: 99%

“…[298] Alternatively, fluorination of benzonitrile with CsCoF 4 was applied to obtain perfluorinated nitrile 452 together with dodecafluorocyclohexane (453) (Scheme 127). [299] Compounds 451 and 452 were used to obtain some other building blocks containing the undecafluorocyclohexyl moiety, namely, cyclo-C 6 F 11 Br, cyclo-C 6 F 11 I (by Hunsdiecker reaction of 451), [300] or cyclo-C 6 F 11 CH 2 NH 2 (by reduction of 452 with LiAlH 4 ). [299] Cyclopropanations of fluorinated alkenes.…”

Section: Chemmedchemmentioning

confidence: 99%

Fluorinated Cycloalkyl Building Blocks for Drug Discovery

et al. 2022

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The review covers various aspects of fluorinated cycloalkyl (C3−C7) building blocks for drug discovery, including their synthesis, key physicochemical properties, and biological and medicinal applications of their derivatives. The discussed synthetic methods include classical nucleophilic fluorinations of various substrates, the addition of fluorine and another heteroatom to double bonds, cycloadditions and other transformations of fluorine‐containing substrates, as well as some newer reactions like fluorination of non‐activated and remotely activated C−H bonds, decarboxylative and deborylative fluorinations, etc. The known data on the effect of introducing the fluorinated cycloalkyl groups on the compound's key in vitro parameters (such as acidity/basicity, lipophilicity, conformational behavior, and short contact capabilities) are surveyed. Finally, applications of fluorinated cycloalkyl building block derivatives in the design of biologically active compounds (including marketed drugs Maraviroc, Ivosidenib, and Sitafloxacin) are covered, with a focus on the fluorination impact.

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The Reaction of Halogens with Silver Salts of Carboxylic Acids

Wilson¹

2011

Organic Reactions

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The action of halogens with dry metallic salts, particularly silver salts of carboxylic acids has merited earlier reviews. It has been pointed out that the halogen used, the ratio of silver salt to halogen, and the presence or absence of other active materials, such as olefins, acetylenes, or readily substituted aromatic rings plays a determining the course of the reactions. Thus it is possible to produce an organic halide containing one less carbon atom than the original acid; esters derived from two molecules of the acid by the loss of one molecule of carbon dioxide; esters of 1,2‐diols or halohydrins; halogenated aromatic compounds; and halogenated acetylenes. These reactions are the subject of this chapter.

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Fluorocarbon Chemistry. IV. The Preparation and Some Reactions of Silver Undecafluorocyclohexanecarboxylate

Cited by 11 publications

References 1 publication

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

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

Fluorinated Cycloalkyl Building Blocks for Drug Discovery

The Reaction of Halogens with Silver Salts of Carboxylic Acids

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