Synthesis of Alkoxythallium(III) Compounds of Olefins and Their Reaction with Copper Halides and Pseudohalides

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Abstract
Some new alkoxythallium(III) compounds of olefins, C6H5C(R1)(OR3)CH2Tl(OCOR2)2 [I], are prepared from styrene and α-methylstyrene with thallium(III) acetate and isobutyrate in various alcohols. I(R1=H) reacts with copper(I) iodide, bromide, chloride, cyanide and thiocyanate to afford the corresponding alkyl halides and pseudohalides, C6H5CH(OR3)CH2X [II], in various organic solvents, acetonitrile being the solvent of choice for the purpose of preparing II. The addition of potassium salt has a remarkable effect in improving the yield of II. The halo- and pseudohalodethallation occur at the position where thallium is attached previously to alkyl carbon. An ionic concerted intermolecular scheme is proposed as a reaction mechanism for the preparation of II. The data of NMR and IR spectra of I are briefly discussed.