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The cannizzaro reaction of benzaldehyde starts with attack of hydroxide ion on the carbonyl carbon which has a electron deficiency. But in the dimethyl amino benzaldehyde, amino group is electron-donating in nature. So, in resonance structures there will be a negative charge on Ortho and para position of the aromatic ring. This negative charge on para ...


The paper by Order and Lindwall [1] agrees with you that the R-T reaction gives indole-3-carboxaldehyde. Since its isolation in 1903 by Hopkins and Cole (1), 3-indole aldehyde has been investigated very little. It was first prepared by Ellinger (2) from indole through the use of the Reimer-Tiemann reaction. This method was improved on later by Boyd and ...

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