Influence of a CF<sub>3</sub> Group on an Adjacent Double Bond. II

Henne, Albert L.; Smook, Malcolm A.; Pelley, Ralph L.

doi:10.1021/ja01166a114

Cited by 16 publications

(2 citation statements)

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“…The copolymerizations were terminated at relatively low conversion. The copolymer formed was dissolved in chloroform, precipitated in methanol, isolated by filtration, and dried at [40][41][42][43][44][45][46][47][48][49][50] °C under vacuum. The composition of the copolymers was determined by elemental analysis and by and 13C NMR.…”

Section: Methodsmentioning

confidence: 99%

Polymerization of methyl α-(trifluoromethyl)acrylate and .alpha.-trifluoromethylacrylonitrile and copolymerization of these monomers with methyl methacrylate

Itô¹,

Miller²,

Willson

1982

Macromolecules

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Section: Methodsmentioning

confidence: 99%

Polymerization of methyl α-(trifluoromethyl)acrylate and .alpha.-trifluoromethylacrylonitrile and copolymerization of these monomers with methyl methacrylate

Itô¹,

Miller²,

Willson

1982

Macromolecules

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“…This is quite surprising since it has been reported that the additionelimination sequence is predominant in the reaction of a-(trifluoromethyl)olefins.10-12 There is one report that describes the SN2 reaction between 3,3,3-trifluoropropene and ethoxide. 13 The gem-difluoride II could further react with a nucleophile to form III which is then immediately converted to monofluoroolefin IV through the MF elimination. As reported in the literature,14,15 the monofluoro compound could further undergo the addition-elimination sequence in the excess of a nucleophile.…”

Section: Resultsmentioning

confidence: 99%

Reaction of α-(trifluoromethyl)styrene with anionic initiators

Itô¹,

Renaldo²,

Ueda³

1989

Macromolecules

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a-(Trifluoromethyl)styrene (Q = 0.43, e = 0.90) does not undergo radical homopolymerization. Anionic polymerization fails to produce appreciable amounts of polymer even in bulk at -78 °C in spite of its high e value. The resistance to anionic polymerization is primarily due to side reactions involving addition-elimination sequences (Sn2') when initiators are nucleophilic enough to add to the 3-carbon of TFMST. Weaker anionic initiators such as pyridine and potassium terf-butoxide that effectively induce polymerization of methyl a-(trifluoromethyl)acrylate (Q = 0.74, e = 2.5) do not react with TFMST. Reactions of TFMST with several anionic initiators are described in detail.

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Rechecking of the equilibrium gas‐phase basicity scale for low‐basicity compounds using fourier transform ion cyclotron resonance spectrometry

Koppel

Anvia

Taft

1994

J of Physical Organic Chem

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Fourier transform ion cyclotron resonance (FT-ICR) spectrometry was used to study and recheck the proton transfer equilibria for a large number of low-basicity compounds, particularly those which are less basic than H,O. The data obtained were used for the construction of a continuous scale of the relative gas-phase basicities between H,S and SO,F,. The present results are compared with the results obtained by McMahon and coworkers using ICR spectrometry and high-pressure mass spectrometric (HPMS) techniques. Satisfactory agreement is found with the existing ICR spectrometric data. The results, however, show unexplained variances with earlier and recent HPMS results that are also not internally self-consistent. The substituent effects for some families of low-basicity compounds (nitriles, carbonyl compounds, ethers and some others) are discussed.

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Influence of a CF₃ Group on an Adjacent Double Bond. II

Cited by 16 publications

References 0 publications

Polymerization of methyl α-(trifluoromethyl)acrylate and .alpha.-trifluoromethylacrylonitrile and copolymerization of these monomers with methyl methacrylate

Polymerization of methyl α-(trifluoromethyl)acrylate and .alpha.-trifluoromethylacrylonitrile and copolymerization of these monomers with methyl methacrylate

Reaction of α-(trifluoromethyl)styrene with anionic initiators

Rechecking of the equilibrium gas‐phase basicity scale for low‐basicity compounds using fourier transform ion cyclotron resonance spectrometry

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Influence of a CF3 Group on an Adjacent Double Bond. II

Cited by 16 publications

References 0 publications

Polymerization of methyl α-(trifluoromethyl)acrylate and .alpha.-trifluoromethylacrylonitrile and copolymerization of these monomers with methyl methacrylate

Polymerization of methyl α-(trifluoromethyl)acrylate and .alpha.-trifluoromethylacrylonitrile and copolymerization of these monomers with methyl methacrylate

Reaction of α-(trifluoromethyl)styrene with anionic initiators

Rechecking of the equilibrium gas‐phase basicity scale for low‐basicity compounds using fourier transform ion cyclotron resonance spectrometry

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Influence of a CF₃ Group on an Adjacent Double Bond. II