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29.6.1.3.3.1 Variation 1: By Oxidation with Thallium(III) Salts

DOI: 10.1055/sos-SD-029-00368

von Angerer, S.; Warriner, S. L.Science of Synthesis, (200729386.

The most important method for the preparation of acetals from alkenes is the oxythallation reaction, which is generally accompanied by rearrangement.[‌625‌‌630‌] The most appropriate thallium(III) salt in terms of reaction time and solubility in organic solvents is thallium(III) nitrate.[‌626‌] This thallium salt can also be used efficiently as a preparation on a solid support (montmorillonite K 10).[‌314‌,‌625‌] When cyclohexene is treated with methanol and thallium(III) nitrate on montmorillonite K 10[‌625‌] or with thallium(III) acetate,[‌627‌] (dimethoxymethyl)cyclopentane (116, X=CH2) is formed in 85% or 62% yields, respectively (Scheme 128). An analogous reaction is observed with dihydropyran, which gives tetrahydrofuran-2-carbaldehyde dimethyl acetal upon treatment with thallium(III) nitrate and methanol.[‌626‌,‌631‌]

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