Synthesis of alcohols via mild oxidation of perfluoroethylstannanes

Falck, John R.; Lai, Jing Yu; Ramana, D. Venkata; Lee, Sang Gyeong

doi:10.1016/s0040-4039(99)00347-0

Cited by 12 publications

(4 citation statements)

References 12 publications

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“…To obtain functionalized perfluoroalkylstannanes, the phenyl group had to be replaced by halogen atoms. Generally, the tin–carbon bond of (perfluoroalkyl)organylstannane derivatives can be cleaved under relatively mild conditions by the use of elemental halogens X 2 or hydrogen halides HX . Jahn et al.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C₂F₅)_4−nSnX_n (X=Ph, Me, Cl, Br, Cp; n=1–3)

Klösener

Wiesemann

Niemann

et al. 2017

Chemistry A European J

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For (pentafluoroethyl)phenylstannanes, (C F ) SnPh (n=1-3), and dimethylbis(pentafluoroethyl)stannane, (C F ) SnMe , a high yield synthesis was developed by the use of LiC F as a C F transfer reagent. The treatment of these products with gaseous hydrogen chloride or hydrogen bromide afforded (C F ) SnX (X=Cl, Br; n=1-3) in good yields. The (pentafluoroethyl)stannanes were fully characterized by H, C, F and Sn NMR, IR spectroscopy and mass spectrometry. The treatment of the (pentafluoroethyl)tin halides (C F ) SnX with 1,10-phenanthroline (phen) led to the formation of the corresponding octahedrally coordinated complexes [(C F ) SnX (phen)], the structures of which were elucidated by X-ray diffraction analyses. The bromostannane (C F ) SnBr reacted with sodium cyclopentadienide to give the (η -cyclopentadienyl)tris(pentafluoroethyl)stannane, (C F ) SnCp, for which single-crystal X-ray diffraction analysis could be performed. The coupling constants J( Sn, C) and J( Sn, F) of all new stannanes are strongly correlated and sensitive to the substitution pattern at the tin atom. For both coupling constants a negative sign could be assigned.

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Section: Resultsmentioning

confidence: 99%

“…The generation of LiC 2 F 5 and its reaction with organotin halides was improved by Falck et al. reaching yields up to 88 % . Reacting donor‐stabilized bis(pentafluoroethyl)cadmium, Cd(C 2 F 5 ) 2 ⋅D, with trifluoroacetato‐ or nitratotrimethylstannane furnished (C 2 F 5 )SnMe 3 in moderate yields .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C₂F₅)_4−nSnX_n (X=Ph, Me, Cl, Br, Cp; n=1–3)

Klösener

Wiesemann

Niemann

et al. 2017

Chemistry A European J

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“…Perfluoroethyl stannane 232a was prepared by the treatment of the corresponding stannyl iodide 231a with perfluoroethyl lithium in 88% yield . In a similar manner, the reaction of tributyltin chloride 231b led to the corresponding fluorinated derivative 232b (Scheme ) .…”

Section: Chemical Properties Of Polyfluorinated Ethanesmentioning

confidence: 99%

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

2015

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“…When substrates are water insoluble, aqueous MeCN is a suitable medium [33]. A very similar system is useful for oxidative cleavage of organostannates containing a perfluoroalkyl group to furnish alcohols [34]. -Formylpyrroles yield 2-pyrrolinones [35].…”

Section: Hydroperoxides In Alkaline Mediamentioning

confidence: 99%

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

Młochowski¹

2011

TOCATJ

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Oxidation of different groups of organic compounds, with hydroperoxides catalyzed by non-heavy metal containing low-molecular-weight compounds and enzymes is reviewed. This article is concentrated mainly on the hydrogen peroxide and tert-butyl hydroperoxide, however other less common hydroperoxides are also mentioned. Since hydroperoxides themselves are inactive toward most of the organic substrates, in situ activation of the oxidant is necessary. For this purpose various activators have been applied in stoichiometric or catalytic amounts. The carboxylic acids, nitriles, amides and urea are representative for the first category. The organocatalysts such as-halo carbonyl compounds, ketones, imines, iminium salts, nitroxyl radicals and polyaminoacids, selenium compounds and enzymes are presented. They are involved in oxygen, and electron transfer processes whose mechanisms are briefly discussed, and their applications in laboratory and industrial synthesis are indicated.

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Synthesis of alcohols via mild oxidation of perfluoroethylstannanes

Cited by 12 publications

References 12 publications

Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C₂F₅)_4−nSnX_n (X=Ph, Me, Cl, Br, Cp; n=1–3)

Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C₂F₅)_4−nSnX_n (X=Ph, Me, Cl, Br, Cp; n=1–3)

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

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Synthesis of alcohols via mild oxidation of perfluoroethylstannanes

Cited by 12 publications

References 12 publications

Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C2F5)4−nSnXn (X=Ph, Me, Cl, Br, Cp; n=1–3)

Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C2F5)4−nSnXn (X=Ph, Me, Cl, Br, Cp; n=1–3)

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

Non-Metal and Enzymatic Catalysts for Hydroperoxide Oxidation of Organic Compounds

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Product

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Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C₂F₅)_4−nSnX_n (X=Ph, Me, Cl, Br, Cp; n=1–3)

Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C₂F₅)_4−nSnX_n (X=Ph, Me, Cl, Br, Cp; n=1–3)