Bromodestannylation reactions of some functionally substituted organotin compounds

Article abstract of DOI:10.1016/0022-328X(89)85139-3

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 Sn-C 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.