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The yields were calculated by weight of the product isolated from duplicate experiments. At the scale (1 mmol) at which the experiments were run, a difference of 6% is not significant. The e.e.'s were measured by VPC on a triacetyl γ-cyclodextrin capillary column, with a precision of 1%. The difference (20%) between the thermal and sonochemical reactions is thus largely above the 2% error margin.
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45
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10644297098
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note
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In Diels-Alder reactions proceeding via oxidatively formed radical-cations ('hole' catalysis), the notation refers to the number of electrons involved: [3+2] if oxidation occurs on the diene and [4+1] if it occurs on the dienophile.
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63
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0027275517
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Weinheim
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In the cases reported by Snider et al. [42], quinones are generated by oxidation of their parent hydroquinones with Fremy's salt or even in situ with silver oxide. The possibility of a non-detected oxidation of the diene by the oxidisers present during the cycloaddition, or remaining as traces, should be taken into account. In particular, traces of Fremy's salt are difficult to remove and this strong monoelectronic oxidiser is activated by sonication; see F. Pautet, P. Formisyn and J. Bourgois, Arch. Pharm. (Weinheim) 326 (1993) 499.
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0000811065
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