Abstract
Bromodestannylation reactions are reported for several functional substituted organotin compounds in carbon tetrachloride and acetonitrile as solvents. The reactions in carbon tetrachloride proceed with a high degree of retention of configuration at the carbon involved in the electrophilic substitution, while in a polar solvent there is an increase in the amount of inversion product formed. The electrophilic cleavage in the β-trialkylstannyl esters takes place with a complete reversal of the normal sequence of SnC bond cleavage by halogens; this is explained by tin assistance. The configuration of some 3-trialkylstannylpropanenitriles, β-bromonitriles and β-bromoesters are assigned. Full 1H, 13C and 119Sn NMR data are given.
Published Version
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