MANNICH REACTIONS OF ARYLTRIALKYLSTANNANES IN APROTIC SOLVENTS

Article abstract of DOI:10.1016/0040-4020(89)80024-9

Aryltributyl- and aryltrimethyl-stannanes react with a range of N,N-dialkylmethylene-imonium salts to afford N,N-dialkylaminomethyl derivatives in good yields.The method can be used to obtain regioisomers that are not available using classical procedures. "In situ" reactions can also be carried out using alkoxydialkylaminomethanes (aminol ethers) and bis(dialkylamino)methanes (aminals) together with chlorotrimethyl- and trichloromethyl-silanes as the source of the electrophile.However, the "in situ" reactions do not afford good yields in the majority of cases, as a result of the inhibition of imonium salt formation by trialkylchlorostannane.