Alkenes oxidation with thallium acetate

Alkenes can also be oxidized with metallic acetates such as lead tetraacetate or thallium(III) acetate " to give bis-acetates of glycols. Oxidizing agents such as benzoquinone, Mn02, or 02, along with palladium acetate, have been used to convert conjugated dienes to l,4-diacetoxy-2-alkenes (1,4 addition). ... 

Mercuric salts induce oxidative rearrangement of cyclic alkenes and give cycloalkane carboxaldehydes. Cyclohexene, for example, gave cyclopentane carboxaldehyde (404) in 53% yield. Acyclic alkenes such as 2-butene can also be oxidized with mercuric sulfate and sulfuric acid, giving 2-butanone in this case.566 Thallium nitrate [T1(N03)3] is an important reagent for the oxidative rearrangement of cyclic alkenes.567 The reaction is not restricted to carbocyclic compounds, but can also be applied to heterocyclic compounds as shown by the oxidation of 3,4-dihydro-277-pyran (405) to the dimethyl acetal (406) in 65% yield.568... 

Nitrosolysis of camphor ethyl acetal with ethanolic ethyl nitrite in sulphur dioxide yields the orthoester oxime (205) which is rapidly dehydrated by excess acetal to the orthoester nitrile which then reacts with sulphur dioxide to form the ester nitrile and diethyl sulphite.Further papers in this section include the full paper on ozonolysis of silyl ethers (Vol. 5, p. 33), another synthesis of camphor-enol trimethylsilyl ether (cf. Vol. 6, p. 41)/°° the conversion of camphor oxime with Grignard reagents into the corresponding imine with no aziridine formation/° the preparation of (206) by treating bornylene with trichloroacetyl isocyanate/ the oxidation of thiocam-phor to the 5-oxide and alkylation in the presence of thallium(i) ethoxide to a/S-unsaturated sulphoxides/ and the free-radical C-3 alkylation of camphor with alkenes. " ... 

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