Fluoroalkyl Iodides Research Articles

Fluoroalkyl Iodide Photodecomposition on Diamond (100) - an Efficient Route to The Fluorination of Diamond Surfaces

ABSTRACTThe photodecomposition of CF3I and C4F9I overlayers at 119 K on diamond (100) surfaces has been shown to be an efficient route to fluorination of the diamond surface. X-ray photoelectron spectroscopy (XPS) has been used for photoactivation as well as for studies of the following processes: the photodecomposition of the fluoroalkyl iodide molecules: the attachment of the photofragments to the diamond surface; and the thermal decomposition of the fluoroalkyl ligands. Chemisorbed CF3groups on diamond (100) decompose by 300 K whereas C4F9groups decompose over the temperature range of 300 K to ∼ 700 K. Both of these thermal decomposition processes produce surface C-F bonds on the diamond surface which thermally decompose over a wide temperature range extending up to 1500 K. Hydrogen passivation of the diamond surface is ineffective in preventing free radical attack from the photodissociated products of the fluoroalkyl iodides. The use of photoactivation of fluoroalkyl iodides for the fluorination of diamond surfaces provides a convenient route compared to other methods involving the direct production of atomic F, molecular fluorine, XeF2, and F containing plasmas.

SnX 2/Al-promoted formylation of per(poly)fluoroalkyl halides with N, N-dimethylformamide

In the presence of catalytic amounts of stannous salts (20 mol%) and aluminium powder, per(poly)fluoroalkyl iodides or bromides react smoothly with DMF under mild conditions to give the corresponding per(poly)fluoroalkyl aldehydes in good to excellent yield. A tin-containing intermediate was obtained. A possible mechanism is proposed.

Barbier-type reaction of fluoroalkyl iodides with aldehydes without activation

Fluoroalkyl iodides react with aldehydes in the presence of zinc in N,N-dimethylacetamide without activation, giving a variety of fluoroalkylated carbinols in 72%–90% yield. The reaction provides a convenient method for the synthesis of these compounds.

Production of Perfluoroalkylated Nanospheres from Buckminsterfullerene

Perfluoroalkylated nanospheres have been prepared by reaction of fullerenes with a variety of fluoroalkyl radicals. The latter are generated by thermal or photochemical decomposition of fluoroalkyl iodides or fluorodiacyl peroxides. Up to 16 radicals add to C(60) to afford easily isolable fluoroalkylated derivatives. The monosubstituted radical adducts were detected by electron spin resonance in the early stages of the fluoroalkylation reactions. These spheroidal molecules are thermally quite stable, soluble in fluoroorganic solvents, chemically resistant to corrosive aqueous solutions, and more volatile than the parent fullerenes. Films of the sublimed material display properties typical for a perfluoroalkylated material.

A novel synthesis of per(poly)fluoroalkyl aldehydes

A novel synthesis of per(poly)fluoroalkyl aldehydes in high yield by the reaction ofper(poly)fluoroalkyl iodides or bromides with dimethylformamide initiated by aPbBr 2(catalyst)/Al bimetal redox system is described.

Stabilities and lifetimes of fluoroalkyl iodide and fluoroallyl iodide collision complexes

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStabilities and lifetimes of fluoroalkyl iodide and fluoroallyl iodide collision complexesRichard W. P. White, David J. Smith, and Roger GriceCite this: J. Phys. Chem. 1993, 97, 10, 2123–2127Publication Date (Print):March 1, 1993Publication History Published online1 May 2002Published inissue 1 March 1993https://doi.org/10.1021/j100112a011RIGHTS & PERMISSIONSArticle Views36Altmetric-Citations11LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (455 KB) Get e-Alerts

Effective fluoroalkylation of aldehydes by σ-perfluoroalkyl-iron compounds

Organoiron compounds with σ-perfluoroalkyl-iron bonds are well-known and common compounds convenient to prepare and handle. However, their application in organic synthesis was restricted to the introduction of fluoroalkyl group only into electron rich organic molecules such as arenes and thiols [I.I. Gerus, Yu.L. Yagupolskii and L.M. Yagupolskii, J. Org. Chem. (Russ. ed.), 21 (1985) 1852; C.G. Krespan, J. Fluor. Chem., 40 (1988) 129]. In this work we have succeeded in the use of the perfluoroalkyltetracarbonyliron iodides for the nucleophilic fluoroalkylation of aldehydes: ▪ The reaction is rapid (∼ 1 h), easy to carry out and does not require an inert atmosphere. From the synthetic point of view it is promising since the starting organoiron compounds are readily prepared from fluoroalkyl iodides and solid substances stable in air.

Polyfluoroalkylation of octa-1,7-diene promoted by dichlorobis-(π-cyclopentadienyl)titanium and iron powder

Per(poly)fluoroalkylation of octa-1,7-diene 1 with per(poly)fluoroalkyl iodides 2 or bromides 4, in the presence of catalytic amounts of dichlorobis(π-cyclopentadienyl)titanium(IV) and iron powder, provides 1:1 linear adducts 3, 5 and/or cyclic products 6 depending on the reactivity of the halides 2 and 4. A radical mechanism is proposed.

A simple and effective method for fluoroalkylation — the addition of fluoroalkyl iodide to olefins in the presence of hydrogen peroxide

AbstractAddition of fluoroalkyl iodides to olefins in the presence of hydrogen peroxide (H2O2) in acetone, acetonitrile or ethanol gave the corresponding 1:1 adducts in good yields. Reaction of fluoroalkyl iodide with diallyl ether (DAE) yielded tetrahydrofuran derivatives. p‐Hydroquinone (p‐HQ) can partly suppress the reaction. A radical initiation mechanism is proposed.

ChemInform Abstract: Studies on Samarium Diiodide Initiated Addition Reaction of Fluoroalkyl Iodides to Alkynes and Its Mechanism.

AbstractSmI2 is found to be an effective initiator in the addition of fluoroalkyl iodides such as (II) to the alkynes (I).

ChemInform Abstract: Palladium‐Catalyzed Double Carbonylation of Alkyl Iodides Bearing a Perfluoroalkyl Group.

AbstractThe fluoroalkyl iodides (I) are carbonylated in the presence of the amines (II) and a Pd catalyst to form the α‐oxo carboxamides (IV), together with the amides (V).

ChemInform Abstract: A New Tin(II) Chloride‐Silver(I) Acetate or ‐Lead(II) Bromide Reagent for the Addition of F‐Alkyl Iodides to Alkenes.

AbstractThe addition of the fluoroalkyl iodides (II) to the alkenes (I) or (IV) is mediated by tin dichloride in the presence of silver acetate or lead dibromide, producing the iodopolyfluoroalkenes (III) or (V).

Studies on samarium diiodide initiated addition reaction of fluoroalkyl iodides to alkynes and its mechanism

Samarium diiodide was found to be an effective initiator in the addition reaction of fluoroalkyl iodides to alkynes. A single electrontransfer radical chain mechanism was proposed for the reaction based on ESR studies and other experimental results.

ChemInform Abstract: Studies on Fluoroalkylation and Fluoroalkoxylation. Part 26. Wilkinson′s Catalyst‐Induced Addition of Fluoroalkyl Iodides to Olefins.

AbstractCoupling of the fluoroalkyl iodides (I) with the terminal olefins (II) in the presence of Wilkinson's catalyst gives the adducts (III).

ChemInform Abstract: Fluoroalkylation and Fluoroalkoxylation. Part 28. Palladium(0)‐Induced Addition of Fluoroalkyl Iodides to Alkenes: An Electron Transfer Process.

AbstractThe palladium‐catalyzed reaction between the fluoroalkyl iodides (I) and the alkenes (II) yields the adducts (III) under mild conditions.

Fluoroalkylation and fluoroalkoxylation. Magnesium single-electron-transfer induced synthesis of 2-fluoroalkylpyrroles

An S RN1 reaction, initiated by single electron transfer from magnesium, provides an efficient method for the regioselective synthesis of 2-fluoroalkylpyrroles from pyrrole and the corresponding fluoroalkyl iodides.

Study on fluoroalkylation and fluoroalkoxylation: 19. Iridium(I)-catalyzed reaction of fluoroalkyl iodides with alkenes and alkynes

Fluoroalkyl iodides reacted with alkenes in the presence of hydridocarbonyltris(triphenylphosphine)iridium (I) to give the corresponding adducts in excellent yields under the mild conditions. Fluoroalkyl iodides reacted also with alkynes to afford E isomer of adducts predominantly. Addition of free radical inhibitor or single electron transfer scavenger to the reaction mixture partially suppressed the reaction. Diallyl ether could trap the fluoroalkyl radical to afford tetrahydrofuran derivative. XPS showed that the valence of Ir (I) rised at the end of the reaction. All findings seem to indicate that the reaction involves a free radical chain mechanism initiated by Ir (I).

Studies on fluoroalkylation and fluoroalkoxylation. Part 26. Wilkinson's catalyst-induced addition of fluoroalkyl iodides to olefins

Addition of fluoroalkyl iodides to olefins in the presence of tris(triphenylphosphine)chlororhodium (I) in benzene or acetonitrile gives the corresponding 1:1 adducts in good yields. The reaction can be suppressed with p-dinitrobenzene (p-DNB) or di-t-butylnitroxide, and tetrahydrofuran derivatives are obtained from the reaction of fluoroalkyl iodides with diallyl ether. A radical chain-reaction mechanism induced by single electron transfer (SET) is proposed.

ChemInform Abstract: Copper‐Induced Telomerization of Tetrafluoroethylene with Fluoroalkyl Iodides.

Abstract In the presence of catalytic amounts of cooper, telomerization of tetrafluoroethylene with fluoroalkyl iodides can be carried out at 80-100°C. As compared with usual high-temperature (∼200 °C) telomerization process, the reaction time required is much shorter.

ChemInform Abstract: Studies on Fluoroalkylation and Fluoroalkoxylation. Regioselective Synthesis of Fluoroalkylated Imidazoles.

AbstractRegioselective fluoroalkylation of sodium imidazolide (I) with the fluoroalkyl iodides and bromides (II) yields the 4‐substituted imidazoles (III).