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3 solutions of the isolated E and Z isomers settled down into an identical mixture (Z:E = 19:81) even in the absence of HI, all these results consistently suggest that the E form of the silylformylation product is generally more thermodynamically stable than the Z form.
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note
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2SiH was in some cases complemented by the use of acetonitrile as a solvent instead of benzene (see entries 7, 8, and 11 in Table 2).
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It is difficult to determine the precise positions of substituents of 19 from NMR spectra. We carried out protodesilylation of 19 by KF in aqueous MeOH at 25 °C for 36 h to give 21 as a single product. Assignment of 21 was unequivocally performed by the comparison of spectral data with those of an authentic sample prepared according to the sequence shown: equation presented
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