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We also tried to synthesize 11 in an "inverse" way by first attaching a phenyl-acetylene moiety to 4b, followed by coupling of the resulting dendritic acetylene branch to 3-tert-butyl-5-bromo salicylic aldehyde by Sonogashira coupling. Unfortunately, mainly homo-coupling of the dendritic acetylene moieties occurred under the coupling conditions, with 11 being formed in only minor amounts.
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77
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note
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In solution generally less than 5 mol% of Mn-Salen are used for the epoxidation reactions. We decided to use 20 mol% of catalyst both for homogeneous and heterogeneous reactions. With the heterogeneous catalysts being recyclable many times, the amount of catalyst employed is not as crucial as under homogeneous conditions!
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18844370727
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note
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In most literature examples, polymer-bound Mn-Salens have been prepared by copolymerization or grafting of a suitable pre-formed Mn-Salen. References [28b] and [31] are examples for loading a polymer-bound Salen with manganese after copolymerization. In contrast to the procedures described in [28b] and [31], we had to use DMF as co-solvent, because our beads do not swell in pure EtOH.
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83
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85046910392
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note
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2O were added, and the organic phase was subjected to CGC analysis.
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84
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84856549574
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A very recent review: K. A. Jørgensen, Angew. Chem. 2000, 112, 3702-3733;
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18844388794
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note
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For determination of the enantioselectivities under homogeneous conditions we used a Salen prepared by condensation of (R,R)-cyclohexane diamine and 3-tert-butyl-5-bromo salicylic aldehyde.
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