Fluorine Resonance Spectra-Structure Correlations for Perhalogenated Propanes.

White, H. F.

doi:10.1021/ac60236a025

Cited by 20 publications

(2 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…IR (cm -1 , thin film): υ CO 1741 (ms), 1687 (ms); υ CF 1216−1096 (vs). NMR (δ, acetone-d 6 ): 13 C{ 1 H} (partial) 114.1 (q, 1 J CF = 287.3 Hz, C F 3 CO), 160.9 (q, 2 J CF = 41.2 Hz, CF 3 C O); 19 F −73.73 (s, 6F, C F 3 CO), −78.10 (t, 4 J FF = 14.0 Hz, 2F, C F 2 I), −79.02 (t, 4 J FF = 10.2 Hz, 3F, C F 3 CF 2 ), −113.44 (m, 2F, C F 2 ), −119.36 (m, 4F, C F 2 ), −119.71 (m, 2F, C F 2 ), −120.55 (m, 2F, C F 2 ), −124.09 (m, 2F, C F 2 ) …”

Section: Methodsmentioning

confidence: 99%

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF₃(CF₂)_n_-₁I(OCOCF₃)₂

Tesevic

Gladysz

2006

J. Org. Chem.

View full text Add to dashboard Cite

Reactions of commercial fluorous alkyl iodides RfnI (1-Rfn; Rfn = CF3(CF2)(n-1); n = 7, 8, 10, 12) with 80% H2O2 and trifluoroacetic anhydride give RfnI(OCOCF3)2 (2-Rfn; 97-89%). These efficiently oxidize aliphatic and benzylic secondary alcohols to the corresponding ketones (92-57%) in the presence of aqueous KBr and absence of organic or fluorous solvents. Bromide ion activates the reagents and/or generates a relay oxidant such as a functional equivalent of Br+. Oxidations are much more rapid (<30 min, 2-R(f8); <70 min, 2-R(f10)) than with other iodine(III) compounds under similar conditions. The coproducts 1-Rfn can be recovered by adding 3-5 volumes of methanol to the reaction mixtures. Fluorous/methanolic liquid/liquid (1-R(f8)) or solid/liquid (1-R(f10)) biphase systems result. The recovered 1-Rfn can be reoxidized to 2-Rfn and reused. Three cycles are conducted with 1-phenyl-1-propanol and 2-R(f10). The propiophenone yields range from 92% to 83% per cycle, and after the final cycle 59-57% of the original charge of the fluorous iodide species is recovered.

show abstract

Section: Methodsmentioning

confidence: 99%

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF₃(CF₂)_n_-₁I(OCOCF₃)₂

Tesevic

Gladysz

2006

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…10 Hz. However, these actually represent four-bond couplings ( 4 J FF , F-C-C-C-F) and not three-bond vicinal couplings ( 3 J FF ), which for some reason are much smaller [71,72]. Overall, the 19 F NMR spectra of fluorous compounds are (like the 1 H spectra of n-alkanes) usually not very informative, and often not reported.…”

Section: Nmr Propertiesmentioning

confidence: 99%

Structural, Physical, and Chemical Properties of Fluorous Compounds

Gladysz

Jurisch

2011

Topics in Current Chemistry

View full text Add to dashboard Cite

The sizes and structures of fluorous molecules are analyzed, particularly with respect to the helical conformations of perfluoroalkyl segments and their phase separation in crystal lattices. Basic molecular properties, bond energies, and special bonding motifs are reviewed. Solubility, adsorption, and related phenomena are treated. Miscibilities of fluorous solvents, and partition coefficients of solutes in fluorous/organic biphase mixtures, are analyzed. Electronic effects and NMR properties are discussed, and some reactions involving the fluorinated parts of fluorous substances are presented.

show abstract

Convenient Modular Syntheses of Fluorous Secondary Phosphines and Selected Derivatives

2005

View full text Add to dashboard Cite

show abstract

Fluorine Resonance Spectra-Structure Correlations for Perhalogenated Propanes.

Cited by 20 publications

References 15 publications

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF₃(CF₂)_n_-₁I(OCOCF₃)₂

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF₃(CF₂)_n_-₁I(OCOCF₃)₂

Structural, Physical, and Chemical Properties of Fluorous Compounds

Convenient Modular Syntheses of Fluorous Secondary Phosphines and Selected Derivatives

Contact Info

Product

Resources

About

Fluorine Resonance Spectra-Structure Correlations for Perhalogenated Propanes.

Cited by 20 publications

References 15 publications

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF3(CF2)n-1I(OCOCF3)2

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF3(CF2)n-1I(OCOCF3)2

Structural, Physical, and Chemical Properties of Fluorous Compounds

Convenient Modular Syntheses of Fluorous Secondary Phosphines and Selected Derivatives

Contact Info

Product

Resources

About

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF₃(CF₂)_n_-₁I(OCOCF₃)₂

Oxidations of Secondary Alcohols to Ketones Using Easily Recyclable Bis(trifluoroacetate) Adducts of Fluorous Alkyl Iodides, CF₃(CF₂)_n_-₁I(OCOCF₃)₂