Journal of Organometallic Chemistry p. 163 - 172 (1985)
Update date:2022-08-11
Topics:
Bongars, Christophe
Bougeard, Peter
Bury, Adrian
Cooksey, Christopher J.
Johnson, Michael D.
et al.
5-Methylhex-5-enylcobaloxime reacts with carbon tetrachloride and with fluorotrichloromethane at 80-100 deg C to give substantially pure 1-methyl-1-(Β,Β,Β-trichloroethyl)- and 1-methyl-1-(β-fluoro-β,β-dichloroethyl)-cyclopentane.Hex-5-enylcobaloxime also gives trichloroethylcyclopentane from carbon tetrachloride, but the yield is dependent on the concentration of carbon tetrachloride.Similar cyclisation to give trichloroethyl- or fluorodichloroethyltetrahydrofuran is observed in the reactions of hex-3-oxo-5-enylcobaloxime with carbon tetrachloride and fluorotrichloromethane.However, no cyclisation was observed in the reactions of the ester, hex-2-one-3-oxo-5-enylcobaloxime, with carbon tetrachloride.These reactions are believed to take place by attack of a polyhalogenomethyl radical at the terminal unsaturated carbon of the organic ligand, followed either by an intramolecular homolytic displacement in which the carbon radical at position-5 attacks carbon-1 with displacement of cobaloxime(II), or by a halogen atom abstraction.
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