Free radical substitution in aliphatic compounds. part XXVI. the gas-phase bromination of halogenocycloalkanes

David S. Ashton; John M. Tedder; John C. Walton; Anthony Nechvatal; Ian K. Stoddart

doi:10.1039/P19730000846

Free radical substitution in aliphatic compounds. part XXVI. the gas-phase bromination of halogenocycloalkanes

David S. Ashton, John M. Tedder^*, John C. Walton, Anthony Nechvatal, Ian K. Stoddart

^*Corresponding author for this work

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

4 Citations (Scopus)

Abstract

The gas-phase bromination of hatogenocyclohexanes gave the expected isomeric bromohalogenocyclohexanes, together with cyclohexene, bromocyclohexane, and traces of trans-1,2-dibromocyclohexane. These latter products were formed as a result of elimination of hydrogen halide from the starting material. The initial halogenocyclohexanes were shown to undergo elimination of hydrogen halide in the presence of hydrogen bromide. Variation of the surface :volume ratio had a pronounced effect on the elimination which suggested that this reaction had a large heterogeneous component. Bromination of chloro- and fluoro-cyclopentane also produced elimination products which were formed as a result of the reaction of hydrogen bromide with the halogenocyclopentane.

Original language	English
Pages (from-to)	846-849
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/P19730000846
Publication status	Published - 1 Jan 1973

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title = "Free radical substitution in aliphatic compounds. part XXVI. the gas-phase bromination of halogenocycloalkanes",

abstract = "The gas-phase bromination of hatogenocyclohexanes gave the expected isomeric bromohalogenocyclohexanes, together with cyclohexene, bromocyclohexane, and traces of trans-1,2-dibromocyclohexane. These latter products were formed as a result of elimination of hydrogen halide from the starting material. The initial halogenocyclohexanes were shown to undergo elimination of hydrogen halide in the presence of hydrogen bromide. Variation of the surface :volume ratio had a pronounced effect on the elimination which suggested that this reaction had a large heterogeneous component. Bromination of chloro- and fluoro-cyclopentane also produced elimination products which were formed as a result of the reaction of hydrogen bromide with the halogenocyclopentane.",

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T1 - Free radical substitution in aliphatic compounds. part XXVI. the gas-phase bromination of halogenocycloalkanes

AU - Ashton, David S.

AU - Tedder, John M.

AU - Walton, John C.

AU - Nechvatal, Anthony

AU - Stoddart, Ian K.

PY - 1973/1/1

Y1 - 1973/1/1

N2 - The gas-phase bromination of hatogenocyclohexanes gave the expected isomeric bromohalogenocyclohexanes, together with cyclohexene, bromocyclohexane, and traces of trans-1,2-dibromocyclohexane. These latter products were formed as a result of elimination of hydrogen halide from the starting material. The initial halogenocyclohexanes were shown to undergo elimination of hydrogen halide in the presence of hydrogen bromide. Variation of the surface :volume ratio had a pronounced effect on the elimination which suggested that this reaction had a large heterogeneous component. Bromination of chloro- and fluoro-cyclopentane also produced elimination products which were formed as a result of the reaction of hydrogen bromide with the halogenocyclopentane.

AB - The gas-phase bromination of hatogenocyclohexanes gave the expected isomeric bromohalogenocyclohexanes, together with cyclohexene, bromocyclohexane, and traces of trans-1,2-dibromocyclohexane. These latter products were formed as a result of elimination of hydrogen halide from the starting material. The initial halogenocyclohexanes were shown to undergo elimination of hydrogen halide in the presence of hydrogen bromide. Variation of the surface :volume ratio had a pronounced effect on the elimination which suggested that this reaction had a large heterogeneous component. Bromination of chloro- and fluoro-cyclopentane also produced elimination products which were formed as a result of the reaction of hydrogen bromide with the halogenocyclopentane.

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DO - 10.1039/P19730000846

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

Free radical substitution in aliphatic compounds. part XXVI. the gas-phase bromination of halogenocycloalkanes

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