Abstract
The orientational preference for the reacting double bonds in the Lewis acid-induced reaction of allylic stannanes and aldehydes has been examined. Model system 1 shows a strong and Lewis-acid independent preference for the synclinal orientation of double bonds. A possible stereoelectronic basis for this preference is discussed. A 13C-NMR spcctroscopic study of the reaction between crotyltrialkylstannanes (9) and acetaldehyde (10), pivaldehyde (11) and 4- t-butylbenzaldehyde (12) in the presence of BF 3·OEt 2 and SnCl 4 is described. The spectroscopic study reveals that with BF 3·OEt 2 only direct addition occurs while with SnCl 4 the pathway (addition vs. metathesis) is stoichiometry and aldehyde dependent. The mechanism of metathesis and chlorostannane isomerization is discussed.
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