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0041827983
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note
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We assume that this side product is formed by hydrolysis of the iminium enolate depicted in Scheme 3, although it is not clear at what stage in the reaction this hydrolysis occurs.
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34
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85082932515
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Diazoketones were prepared as described in refs 1 b and 2c. Imines derived from aromatic aldehydes were prepared according to Texier-Boullet, F. Synthesis 1985, 679. Imines derived from acrolein or crotonaldehyde were prepared analogously, but were distilled prior to use.
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Synthesis
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Texier-Boullet, F.1
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35
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0042328921
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note
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The MW experiments were performed in an MLS-ETHOS 1600 apparatus (MLS GmbH) using a flask equipped with a reflux condenser (mounted outside the apparatus) or in a Teflon autoclave (100 mL). A control and monitoring software (ETHOS PC98) was used, and the temperature was monitored via a temperature sensor.
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36
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0042328920
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Patai, S., Ed.; John Wiley & Sons: Chichester
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Commercially available crotonaldehyde as used for imine formation contained ∼4% Z-isomer, which was not separated before use. An E → Z isomerization at elevated temperatures has been reported: Slayden, S. W. In The Chemistry of Double-Bonded Functional Groups. Supplement A3. Part 1; Patai, S., Ed.; John Wiley & Sons: Chichester, 1997; p 537.
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Slayden, S.W.1
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(b) Varma, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 2039.
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Kumar, S.3
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39
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0042328919
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note
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The rates of the thermal and the MW-assisted formation of β-lactam 3 have been compared. After 5 min 80% conversion for the thermal reaction and 85% for the MW reaction, respectively were detected, i.e., identical rates within the limits of experimental error. The photochemical reaction is not comparable in this context, since it is, as a result of increasing extinction, dependent on the concentration of the starting materials.
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