Triorganothallium compounds

Marko and co-workers recently found a unique property of triorganothallium compounds (TOT) their ability to react preferentially with enones (Scheme 2-24) [54], One of the most striking observations is that selectivity of the process increases as the substrate becomes more conjugated and the intrinsic reactivity of the carbonyl function decreases. This chemical event can be interpreted by the single electron transfer from the thallium species to enones, followed by recombination of the resulting radical species 1-5 and 1-6. 

Owing to the weakness of the Tl-C bonds, triorganothallium derivatives are highly reactive compounds. Trimethyl-and triphenylthallium react with mercury to form the corresponding diorganomercury derivatives and elemental thallium (equation 9). ... 

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