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Unless starting from the α,β-dialkylated or β,β-dialkylated α,β-unsaturated acids.
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Unless starting from the α,β-dialkylated or β,β-dialkylated α,β-unsaturated acids.
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We exhaustively tested many classical conditions to prepare acid chlorides, but the only condition that provided acceptable yields of 1 was refluxing the carboxylic acid with freshly distilled oxalyl chloride in chloroform.
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We exhaustively tested many classical conditions to prepare acid chlorides, but the only condition that provided acceptable yields of 1 was refluxing the carboxylic acid with freshly distilled oxalyl chloride in chloroform.
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Only the E isomer was detected.
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Only the E isomer was detected.
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35
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55249104505
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For a precedent that shows a similar type of coupling between ethyldiazoacetate and aldehydes, see
-
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Very recently, a new procedure of diazoketone syntheses employing only one equivalent of diazomethane has been described
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Very recently, a new procedure of diazoketone syntheses employing only one equivalent of diazomethane has been described: Pace, V.; Verniest, G.; Sinisterra, J.; Alcantara, A. R; De Kimpe, N. J. Org. Chem. 2010, 75, 5760
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78650868225
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Lowering the reaction scale by too much and/or not using freshly prepared diazomethane caused the yield to drop to 46-50%.
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Lowering the reaction scale by too much and/or not using freshly prepared diazomethane caused the yield to drop to 46-50%.
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