Free radical rearrangements of organocobaloximes: alkynyl to cycloalkylidene and hexenyl to cyclopentylmethyl |
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Authors: | Peter Bougeard Christopher J Cooksey Michael D Johnson Melanie J Lewin Stewart Mitchell Paul A Owens |
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Institution: | Department of Chemistry, University College, 20 Gordon Street, London WC1H 0AJ Great Britain |
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Abstract: | Under irradiation by tungsten light in pyridine solution, several substituted alkylcobaloximes undergo rearrangement to more stable substituted alkyl- or alkenyl-cobaloximes. When the same reactions are carried out in the presence of carbon tetrachloride or chloroform, no rearranged organocobaloximes are obtained, but a variety of organic products are obtained derived from the interception of transient organic radicals by the halogenated solvent. The rearrangements are rationalised in terms of a reversible homolysis of the carbon-cobalt bond, rearrangement of the organic radical and recapture by the cobalt(II) fragment to give complexes that are more stable to irradiation than their precursors. |
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