Original reactions of α,α-dithio aryl alkanes with butyllithiums

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Thioacetals derived from aroamtic ketones react with butyllithiums already -78°C and produce via a redcutive process the corresponding α-thiobenzyllithiums in high yields. The same reaction also takes place selectively, under suitable conditions, with the thioacetals deived from benzaldehyde on which a competing metallation reaction is also possible. These observations clearly show that thioacetal functionality is not asutiable protecting group against alkyllithiums for aromatic carbonyl compounds. © 1991.




Krief, A., Kenda, B., & Barbeaux, P. (1991). Original reactions of α,α-dithio aryl alkanes with butyllithiums. Tetrahedron Letters, 32(22), 2509–2512. https://doi.org/10.1016/S0040-4039(00)74368-1

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