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The compound shown here is an example of the basic 2-amino-1,3-cyclohexadiene side-product in the Knoevenagel condensation of benzaldehyde and ethyl acetoacetate (entry 1 in Table 1).
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A low crosslinking of 2% DVB (DOWEX50X2) is absolutely necessary. Application of macroporous DOWEX50X8 (8% DVB) led to yields <1% under otherwise identical reaction conditions.
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For a graphical representation see the Supporting Information.
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For an on-bead FTIR analysis of the reaction of diisopropyl azodicarboxylate (DIAD) with scavenger resin 11 see the Supporting Information.
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