Reactions of some perhaloarenes with metals and metal halides

Webb, A.F.; Gilman, Henry

doi:10.1016/s0022-328x(00)80121-7

Cited by 12 publications

(2 citation statements)

References 7 publications

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“…In the second approach, bromopentafluorobenzene reacted with lithium amalgam and 4 was allowed to react with N-methylformanilide to give pentafluorobenzaldehyde (1) in the 61% yield (Scheme 1). The preparation of 4 as a starting material for preparation of pentafluorobenzaldehyde (1) was described in other papers [4][5][6][7].…”

Section: History and Synthesis Of Pentafluorobenzaldehydementioning

confidence: 99%

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pažitný

Solčan

Végh

2009

Journal of Fluorine Chemistry

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Section: History and Synthesis Of Pentafluorobenzaldehydementioning

confidence: 99%

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pažitný

Solčan

Végh

2009

Journal of Fluorine Chemistry

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“…Synthesis and Characterization of 1•Sb3F16 and 2. 1•Sb3F16 was synthesized in a 4-step reaction starting from commercially available bromopentafluorobenzene A via the formation of the known perfluorotolane B [40][41] and tetrakis(pentafluorophenyl)tetracyclone C (Scheme 2). 42 Temperature-controlled reaction of C with C6F5MgBr gave pentakis(pentafluorophenyl)cyclopentadienole D in good yield (58 %).…”

Section: Resultsmentioning

confidence: 99%

Structural Characterization and Reactivity of a Room Temperature-Stable, Antiaromatic Cyclopentadienyl Cation Salt

Schulte

Wölper

Rupf

et al. 2023

Preprint

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The singlet states of cyclopentadienyl (Cp) cations are considered as true prototypes of an antiaromatic system. Due to their high reactivity, their isolation in the solid state as a salt has so far failed. We present here the synthesis of the first room temperature-stable Cp cation salt Cp(C6F5)5Sb3F16 (1·Sb3F16) by single electron oxidation of the corresponding Cp radical Cp(C6F5)5∙ (2) with either an excess of XeF2 and SbF5·SO2 or by hydroxide abstraction from Cp(C6F5)5OH (D) with SbF5·SO2 in hexafluorobenzene. 1·Sb3F16 was characterized by sc-XRD, SQUID, UV-vis, and EPR spectroscopy. Although the aromatic triplet state of the Cp(C6F5)5 cation 1 is energetically favored in the gas phase according to quantum chemical calculations, the coordination of the cation by either Sb3F16⁻ (1a·Sb3F16) or C6F6 (1b·Sb3F16) in the crystal lattice stabilizes the antiaromatic singlet state, which is present in the solid state. The calculated hydride and fluoride ion affinities of 1 are higher than those of the tritylium cation C(C6F5)3+. In addition, results from reactions of 1·Sb3F16 with CO, which most likely yields the corresponding carbonyl complex, and 2 with selected model substrates (Cp2Fe, (Ph3C∙)2, and Cp*Al) are presented.

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Substitution Reactions Using Organocopper Reagents

Posner

2011

Organic Reactions

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Carbon‐carbon sigma‐bond formation one of the most fundamental operations in organic chemistry, is often accomplished by interaction of an organometallic reagent with an organic substrate having a suitable leaving group. Selective substitution of halogens and of alcohol derivatives by various hydrocarbon groups in many different types of organic substrates has been achieved most successfully using organocopper reagents. The wide scope and effectiveness of these reagents in coupling with halides and alcohol derivatives have made formation of the unsymmetrical coupling product R‐R' a useful reaction in organic synthesis, allowing efficient and specific substitution of X by alkyl, alkenyl, alkynyl, or aryl groups. Because selective coupling between organic substrate and organocopper reagent is usually achieved more effectively by stoichiometric than by catalytic organocopper reagents, and more effectively still by organocuprates(I) than by mono‐copper or by complexed organocopper reagents, the emphasis in this chapter is on organocuprates (I). Consideration is given to possible mechanisms of substitution reactions using organocopper reagents, to scope, limitations, and synthetic utility of these reactions, and to optimal experimental considerations for their application.

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Reactions of some perhaloarenes with metals and metal halides

Cited by 12 publications

References 7 publications

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Pentafluorobenzaldehyde and its utilizing in organic synthesis

Structural Characterization and Reactivity of a Room Temperature-Stable, Antiaromatic Cyclopentadienyl Cation Salt

Substitution Reactions Using Organocopper Reagents

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