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3743139655
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More accurate analytical methods (GC or HPLC) cannot be adopted since products 2 decomposed at the high temperatures necessary for GC, and we were unable to attain sufficient separation of the compounds by HPLC.
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45
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3743080642
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note
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Retroaldolic reaction was observed when nonvolatile products were formed. For example, in the reaction of 1ca with MeMgBr we found about 8% yield of propiophenone among the reaction products, and in the reaction of 1aa with PhMgBr, benzyl alcohol was recovered in about 6% yield from the attack of the Grignard reagent on formaldehyde.
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In these cases, if the temperature of the reaction mixture is allowed to rise above - 20 °C, then color of the mixture turns from yellow to dark brown and, after the usual work-up, large amounts of intractable sticky and insoluble products were recovered, which are probably due to polymerization processes.
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* indicate that diastereomeric compounds are obtained as racemates. We prefer this terminology to avoid the ambiguities that could arise from the use of syn-anti or erythro-threo.
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