Free-radical addition to olefins. Part VII. Addition of trichloromethyl radicals to chloro-olefins

D. P. Johari, H. W. Sidebottom, J. M. Tedder, J. C. Walton*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The photochemically induced addition of bromotrichloromethane to a series of chlorine-substituted ethylenes has been studied in gas-phase experiments. Addition to a carbon atom of the olefin not carrying a chlorine atom leads to formation of a normal adduct. When the addition of trichloromethyl radicals or bromine atoms occurs at a carbon atom carrying a chlorine atom the major products are CCl3CX=CX2 and BrCX=CX2 respectively, where CXCl=CX2 represents the original chloro-ethylene. The rate of trichloromethyl radical addition to a chlorine-substituted site is slower than the rate of addition at =CF2 and much slower than addition to =CH2. Arrhenius parameters for the addition of CCl 3· to the =CH2 end of vinyl chloride have been measured: k(=CH2) = (1.1 ± 0.4) × 107 exp(-3400 ± 200)/RT

Original languageEnglish
Pages (from-to)95-99
Number of pages5
JournalJournal of the Chemical Society B: Physical Organic
DOIs
Publication statusPublished - 1 Jan 1971

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