ChemInform Abstract: Ozonization of Perfluoroolefins in Trifluoroacetic Acid Solution.

Моисеева, Н. И.; Гехман, А. Е.; Rumyantsev, E.S.; Klimanov, V. I.; Моисеев, И. И.

doi:10.1002/chin.199005098

ChemInform

1990

DOI: 10.1002/chin.199005098

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ChemInform Abstract: Ozonization of Perfluoroolefins in Trifluoroacetic Acid Solution.

Н. И. Моисеева

А. Е. Гехман

E.S. Rumyantsev

et al.

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“…Accordingly, in the first step of our optimized procedure alcohol 1 was converted to olefin 2 using an organolithium reagent . Then, in the next step we used ozone, a hazardous but clean oxidant, to cleave 2 at the double bond, since previous studies have demonstrated its effectiveness in different solvents. , …”

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A Novel Strategy for the Synthesis of ω-Functionalized Perfluoroalkyl Iodides

et al. 2001

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[reaction: see text] The applicability of telomeric alcohols, H(CF(2)CF(2))(n)()CH(2)OH, for the synthesis of omega-functionalized F-alkylating reagents, I(CF(2)CF(2))(n-1)CH(2)OAc (6, n = 5), is demonstrated. The key steps of this optimized method are the "activation" of the HCF(2)- terminus in a lithiation process yielding olefin 2 [(Z+E)-BuCF=CF(CF(2)CF(2))(4)CH(2)OH, 86%] and a successive ozonation reaction in trifluoroethanol media affording ester 3b [CF(3)CH(2)O(2)C(CF(2)CF(2))(4)CH(2)OH, 93%]. Highly stereospecific ozone cleavage of the (E)-2 isomer was observed in methanol due to the competitive oxidation of the solvent.

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A Novel Strategy for the Synthesis of ω-Functionalized Perfluoroalkyl Iodides

et al. 2001

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“…[3][4][5] The resulting perfluorocarboxylic acid fluorides were identified by 19F NMR and GLC, but were not isolated. Perfluorocyclohexene does not change under these conditions.…”

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Ozonolysis of perfluoroalkenes and perfluorocycloalkenes

et al. 1997

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Ozonolysis of 1-methoxyperfluorocyclobutene in Freon-l 13 followed by hydrogenation of the reaction products gave methyl hydrogen perfluorosuccinate. Under similar conditions, perfluorooct-I-and -2-enes and 4-trifluoromethyl-1,i, 1,2,3,4,5,5,5-nonafluoropent-2-ene were converted into perfluorinated heptanoic, hexanoic, and isobutyrie acids, respectively.Key words: pertluorocyetoalkenes, ozonolysis, reduction, Lindlaz catalyst, perfluorocarboxylic acids.Ozonolysis of perfluoroalkenes has been accomplished only for lower homologs of this series, l,z Conjugated oxidation of perfluorooct-l-ene and perfluorooct-2-ene and CF3CO2H in the process of their joint ozonation has also been reported. 3-5 The resulting perfluorocarboxylic acid fluorides were identified by 19F NMR and GLC, but were not isolated. Perfluorocyclohexene does not change under these conditions. 5We developed a method of ozonolysis of perfluoroalkenes in Freon-ll3. 6 Under these conditions, perfluorocyclobutene (1) yields only traces of an oxygencontaining product. However, t-methoxyperfluorocyclobutene (2) prepared from olefin t by nucleophilic substitution of the vinylic fluorine atom does undergo the ozonolysis. 7-9 Treatment of 2 with a fivefold excess of O 3 followed by hydrogenation of the ozonolysis products over the Lindlar catalyst, i.e., under the conditions of "reductive ozonolysis", 1 yields methyl hydrogen tetrafluorosuccinate (3) in a yield of 60% instead of the expected ester of perfluorosuccinaldehydic acid. Ozonolysis of perfluoroaIkenes 4--6 under the same conditions leads to perfluorocarboxylic acids (7--9) in 86, 80, and 74% yields, respectively. The structures of compounds 3 and 7--9 were confirmed by spectral methods. The IR spectra of perfluorinated acids 3, 7--9 are characterized by regular displacement of the band of the carbonyl group to shorter wavelen~hs (v 1760--1770 cm-l), which is due to the decrease in its electron density caused by highly electronegative fluorine atoms, l~ The 13C NMR spectrum of compound 3 exhibits two triplets (8 160. 48. The signals in the 13C NMR spectrum of compound 3 were assigned using a pulse sequence of J-modulated spin echo (JMOD). The tH NMR spectrum of compound 3 contains two singlets with a ratio of intensities of 3: 1. The narrow singlet at 8 3.94 corresponds to the methoxycarbonyl group, while the broadened singtet is due to the carboxyl group; the position of this signal (8 7.8--11.35) changes as a function of the concentration of the substance (12.5--50 mg mL -1) and the temperature of the solution (-55 to 50 ~ Increases in the temperature and dilution of the solution are favorable for the cleavage of the intramolecular hydrogen bond, which leads to an upfield shiR of the signal of the carboxyl group in the spectrum of compound 3. II In the mass spectra of both the initial compound 2 and the product of its ozonolysis 3, the largest mass number corresponds to an ion with m/z 174. However, in the case of alkene 2, this is the molecular ion (its molecular formula is CsHsF50), whereas in th...

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ChemInform Abstract: Ozonization of Perfluoroolefins in Trifluoroacetic Acid Solution.

Cited by 2 publications

References 0 publications

A Novel Strategy for the Synthesis of ω-Functionalized Perfluoroalkyl Iodides

A Novel Strategy for the Synthesis of ω-Functionalized Perfluoroalkyl Iodides

Ozonolysis of perfluoroalkenes and perfluorocycloalkenes

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