Phenyliodine(V) fluorides

Hoyer, Sevim; Seppelt, Konrad

doi:10.1016/j.jfluchem.2003.12.004

Cited by 20 publications

(29 citation statements)

References 35 publications

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“…(1)) which displayed 19 F resonances at À86.5 (s, t 1/2 = 30 Hz, 1F, BrF), À128.5 (m, 2F, F 2,6 ), Perfluoroorganobromine(III) difluoride Perfluoroorganoiodine(III) difluoride Perfluoroorganoiodine(V) tetrafluoride Fluoride abstraction Perfluoroorganyl(fluoro)halonium cations NMR spectroscopy…”

Section: Resultsmentioning

confidence: 99%

“…The chemical shifts are referenced to TMS ( 13 C), and CCl 3 F ( 19 F, with C 6 F 6 as secondary reference (À162.9 ppm)), respectively. The composition of the reaction mixtures and the yields of products were determined by 19 F NMR spectroscopy using the internal quantitative standards C 6 F 6 or C 6 H 5 CF 3 . Polyfluorocycloalkenes 5, 6, 7, and 9 were identified by 19 F NMR spectroscopy [31].…”

Section: Methodsmentioning

confidence: 99%

“…Bubbling of BF 3 (excess) into a solution of 2 in PFP at À20 8C or stirring a CH 2 Cl 2 solution of 2 at À40 8C under the pressure of BF 3 (excess) resulted in a yellow precipitate (2b). The solution of the latter in cold (À40 8C) MeCN showed 19 9)). This information suggested to examine the reaction of C 6 F 5 BrF 2 with aHF.…”

Section: Introductionmentioning

confidence: 94%

“…The broad signals of the counteranion [Sb n F 5n+1 ] À were located at À88 and À110 ppm (cf. [18] [19]. (11) Neither the chemical shifts nor the magnitudes of the J(F,F) couplings were changed when the solution of 3d was kept at À20 8C (30 min) and at 0 8C (30 min).…”

Section: Reaction Of C 6 F 5 If 4 With Fluoride Acceptorsmentioning

confidence: 99%

“…Fluoride abstraction from C 6 F 5 IF 2 and C 6 F 5 IF 4 under the action of SbF 5 in SO 2 ClF at low temperatures was reported to give solutions of [C 6 F 5 IF]Y [17] and [C 6 F 5 IF 3 ]Y [18], respectively. Seppelt prepared the salt [C 6 H 5 IF 3 ][SbF 6 ] from C 6 H 5 IF 4 and SbF 5 in anhydrous HF (aHF) at À30 8C and characterized it by X-ray structural analysis, 1 H, 19 F NMR, and Raman spectra [19]. In all cases, the salts [ArIF nÀ2 ][Sb m F 5m+1 ] (n = 3, 5) were intrinsically unstable and decomposed above À20 to 0 8C to unknown products.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

A widely varying range of products in reactions of C6F5BrF2, C6F5IF2, and C6F5IF4 with Lewis acids of different strength

Frohn

Bailly

Welting

et al. 2009

Journal of Fluorine Chemistry

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

Section: Reaction Of C 6 F 5 If 4 With Fluoride Acceptorsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

A widely varying range of products in reactions of C6F5BrF2, C6F5IF2, and C6F5IF4 with Lewis acids of different strength

Frohn

Bailly

Welting

et al. 2009

Journal of Fluorine Chemistry

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Structural Chemistry of Hypervalent Iodine Compounds

Justik

2018

Patai's Chemistry of Functional Groups

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To quote the modernist architectural mantra: “form follows function.” HVI compounds possess highly unique geometric features, which are highly tunable toward reactivity, making them impressively useful tools in modern synthetic chemistry. This chapter will endeavor to discuss the latest investigations into the structures of λ 3 ‐ and λ 5 ‐iodanes and revisit the past work with fresh insight. A new taxonomy for organizing hypervalent iodine compounds by structure will be introduced. The latest understanding of halogen bonding will be applied to the long‐observed “secondary‐bonding” interactions present in many solid‐state structures. These interactions are now understood to play a key role in the opening stages of reaction mechanisms involving hypervalent iodine reagents, especially in arylation chemistry. The X‐ray crystallographic data from a representative scope of iodanes will be complied in one work, as an easily accessible reference for those new to the field or those cogitating new possible structural motifs to solve synthetic challenges.

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NMRof Hypervalent Iodine Compounds

Shafir

2018

Patai's Chemistry of Functional Groups

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Nuclear magnetic resonance (NMR) spectroscopy has played a key role in the rise of modern high‐valent halogen chemistry, especially for gaining solution‐state information on the corresponding organic derivatives. This chapter is focused on those aspects of NMR that have somehow proven specific to this family of compounds, including instances of abnormal chemical shifts, the highly electron‐withdrawing nature of the iodane group, and the presence of highly ionic hypervalent bond. In addition, the essay includes aspects that have had a particular impact on the development of this area of chemistry. The chapter is divided into six sections, with Section I introducing some of the general aspects of the NMR spectroscopy of high‐valent organoiodine species, including the normal halogen dependence (NHD) explanation for certain chemical shift abnormalities, the general iodine oxidation state influence on 1 H and 13 C chemical shifts, and certain challenges of solution‐state measurements for this class of compounds. Section II presents a discussion on the difficulty of directly measuring the halogen chemical shifts due to the nucleus' high quadrupole moments, especially for 127 I. Sections III and IV contain a discussion of some of the most relevant 13 C and 19 F NMR studies, including the key contributions of these two techniques to the understanding of the physical organic chemistry aspects of high‐valent halogen derivatives. Section V is dedicated to the NMR characterization via the less‐common nuclei, specifically 11 B, 31 P, 29 Si, and 17 O NMR, and includes a discussion of the role played by 17 O NMR in establishing the dynamic nature of certain key high‐valent carboxylates. Finally, Section VI presents a series of selected studies in which NMR is used to shed light on the mechanism of processes involving high‐valent iodine reagents.

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Phenyliodine(V) fluorides

Cited by 20 publications

References 35 publications

A widely varying range of products in reactions of C6F5BrF2, C6F5IF2, and C6F5IF4 with Lewis acids of different strength

A widely varying range of products in reactions of C6F5BrF2, C6F5IF2, and C6F5IF4 with Lewis acids of different strength

Structural Chemistry of Hypervalent Iodine Compounds

NMRof Hypervalent Iodine Compounds

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