Free radical addition to olefins. Part 8. - Addition of n-heptafluoropropyl radicals to fluoro-ethylenes

J. M. Tedder; J. C. Walton; K. D.R. Winton

doi:10.1039/F19726800160

Free radical addition to olefins. Part 8. - Addition of n-heptafluoropropyl radicals to fluoro-ethylenes

J. M. Tedder^*, J. C. Walton, K. D.R. Winton

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The light-induced addition of perfluoropropyl iodide to fluoro-ethylenes in the gas phase C₃F₇·+RCH=CH₂→C ₃F₇CH₂ĊHR (2) has been studied, and activation parameters determined by a competitive method. The corresponding differences found are: ΔE₂(kcal mol^-1) Δ(log A₂)(l. mol^-1 s^-1) C*F₂=CFH: C*FH=CF₂ 1.04±0.36 0.07±0.02 C*F ₂=CH₂:C*H₂=CF₂ 5.52±1.06 -0.89±0.11 C*FH=CH₂:C*H ₂=CFH 2.25±0.66 0.18±0.06 C*H₂=CFH: C*H₂=CH₂ 0.79±0.43 0.09±0.04 C*H₂=CF₂:CH₂=CH₂ 2.67±0.30 -0.66±0.02 C*FH=CF₂:C*H ₂=CF₂ 0.38±0.22 0.44±0.02 C*F ₂=CF₂:C*H₂=CH₂ 4.67±1.50 -1.56±0.12. The most striking feature is the similarity to the results for addition of bromotrichloromethane to the same olefins. Relationships between activation energies and some theoretical quantities are discussed.

Original language	English
Pages (from-to)	160-166
Number of pages	7
Journal	Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases
Volume	68
DOIs	https://doi.org/10.1039/F19726800160
Publication status	Published - 1 Dec 1972

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title = "Free radical addition to olefins. Part 8. - Addition of n-heptafluoropropyl radicals to fluoro-ethylenes",

abstract = "The light-induced addition of perfluoropropyl iodide to fluoro-ethylenes in the gas phase C3F7·+RCH=CH2→C 3F7CH2ĊHR (2) has been studied, and activation parameters determined by a competitive method. The corresponding differences found are: ΔE2(kcal mol-1) Δ(log A2)(l. mol-1 s-1) C*F2=CFH: C*FH=CF2 1.04±0.36 0.07±0.02 C*F 2=CH2:C*H2=CF2 5.52±1.06 -0.89±0.11 C*FH=CH2:C*H 2=CFH 2.25±0.66 0.18±0.06 C*H2=CFH: C*H2=CH2 0.79±0.43 0.09±0.04 C*H2=CF2:CH2=CH2 2.67±0.30 -0.66±0.02 C*FH=CF2:C*H 2=CF2 0.38±0.22 0.44±0.02 C*F 2=CF2:C*H2=CH2 4.67±1.50 -1.56±0.12. The most striking feature is the similarity to the results for addition of bromotrichloromethane to the same olefins. Relationships between activation energies and some theoretical quantities are discussed.",

author = "Tedder, {J. M.} and Walton, {J. C.} and Winton, {K. D.R.}",

year = "1972",

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AU - Tedder, J. M.

AU - Walton, J. C.

AU - Winton, K. D.R.

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N2 - The light-induced addition of perfluoropropyl iodide to fluoro-ethylenes in the gas phase C3F7·+RCH=CH2→C 3F7CH2ĊHR (2) has been studied, and activation parameters determined by a competitive method. The corresponding differences found are: ΔE2(kcal mol-1) Δ(log A2)(l. mol-1 s-1) C*F2=CFH: C*FH=CF2 1.04±0.36 0.07±0.02 C*F 2=CH2:C*H2=CF2 5.52±1.06 -0.89±0.11 C*FH=CH2:C*H 2=CFH 2.25±0.66 0.18±0.06 C*H2=CFH: C*H2=CH2 0.79±0.43 0.09±0.04 C*H2=CF2:CH2=CH2 2.67±0.30 -0.66±0.02 C*FH=CF2:C*H 2=CF2 0.38±0.22 0.44±0.02 C*F 2=CF2:C*H2=CH2 4.67±1.50 -1.56±0.12. The most striking feature is the similarity to the results for addition of bromotrichloromethane to the same olefins. Relationships between activation energies and some theoretical quantities are discussed.

AB - The light-induced addition of perfluoropropyl iodide to fluoro-ethylenes in the gas phase C3F7·+RCH=CH2→C 3F7CH2ĊHR (2) has been studied, and activation parameters determined by a competitive method. The corresponding differences found are: ΔE2(kcal mol-1) Δ(log A2)(l. mol-1 s-1) C*F2=CFH: C*FH=CF2 1.04±0.36 0.07±0.02 C*F 2=CH2:C*H2=CF2 5.52±1.06 -0.89±0.11 C*FH=CH2:C*H 2=CFH 2.25±0.66 0.18±0.06 C*H2=CFH: C*H2=CH2 0.79±0.43 0.09±0.04 C*H2=CF2:CH2=CH2 2.67±0.30 -0.66±0.02 C*FH=CF2:C*H 2=CF2 0.38±0.22 0.44±0.02 C*F 2=CF2:C*H2=CH2 4.67±1.50 -1.56±0.12. The most striking feature is the similarity to the results for addition of bromotrichloromethane to the same olefins. Relationships between activation energies and some theoretical quantities are discussed.

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ER -

Free radical addition to olefins. Part 8. - Addition of n-heptafluoropropyl radicals to fluoro-ethylenes

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