It has been shown by NMR spectroscopy that aldehydes dissolved in HF‐BF 3 are completely protonated at −80°. The extreme low‐field chemical shift of the added proton demonstrates that the carbon‐oxygen bond in these protonated aldehydes remains largely a double bond. At higher temperatures deprotonation by fluoride anions takes place. Line‐broadening measurements showed this process to be diffusion‐controlled.
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H. Hogeveen (1967) studied this question.
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