Reactions of Aldehyde Caused by Tris(trimethylsiloxy)aluminum

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Abstract
Reactions of n-butyraldehyde caused by tris(trimethylsiloxy)aluminum were examined and compared with those caused by aluminum t-butoxide. In the Tishchenko reaction of aldehyde caused by aluminum t-butoxide, the t-butoxy group was first transferred from aluminum to the carbonyl group of n-butyraldehyde to produce t-butyl n-butyrate. On the other hand, we observed no formation of trimethylsilyl n-butyrate by the transfer of the trimethylsiloxy group to n-butyraldehyde. However, esters of the n-butyric acid of n-butanol and the glycol derived from the aldol of n-butyraldehyde were found in the system with tris(trimethylsiloxy)aluminum: their formation was ascribed to the aluminum alkoxide species which was first formed between tris(trimethylsiloxy)aluminum and the aldol of n-butyraldehyde. The above assumption has been supported by the finding that aluminum t-butoxide caused the Tishchenko reaction of benzaldehyde, producing benzyl benzoate almost quantitatively, whereas tris(trimethylsiloxy)aluminum did not cause any change because aldol condensation was impossible for benzaldehyde.

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