Abstract
Two hgh yield synthetic methods are described for the preparation of alkyl, dialkyl, aryl and diaryl ketene bis(trialkylsilyl)acetals. One is by reaction of αmetalated trimethylsilyl carboxylates with trimethylchlorosilane (TMCS) and the otehr is by inteaction of dianions of carboxylic acids and TMCS. The dianion of cyclopropane carboxylic acid and TMCS gave C-silated ester in 90% yield. Pyrolysis of diphenyl ketene bis(trialkylsilyl) acetals to diphenyl ketene and bis(trialkylsily) ethers has been shown by crossover experiments to proceed intermoleculary. Pyrolysis of monosubstituted and dialkyl ketene (trimethylsilyl) acetals gave ketene-ketene acetal addition products (III) which on solvolysis afforded β-keto acids in high yield. NMR and mass spectral data are given for many of the compounds.
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