The Pd-mediated oxidation of unsaturated thioacetals gives either allyl or vinyl esters, depending on the substrate structure. We report the characterization of a range of sulfur-stabilized palladium intermediates via a combined computational and experimental NMR approach, demonstrating that the oxidation proceeds via two divergent reaction mechanisms. We were also able to synthesize an unusual σ-bound Pd complex, via acetoxypalladation of an unsaturated dithiane, which was characterized by X-ray crystallography.
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Mann et al. (2011) studied this question.
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