Organometallic reactions. Part V. Trialkylstannylation of amides

Abstract

The N-trialkylstannyl derivatives of a number of amido-compounds have been prepared by the general reaction (R₃Sn)₂O + 2R′NH·CO·X → 2R₃Sn·NR′·CO·X + H₂O. If X is a more electronegative group, the reaction of secondary amido-compounds follows the course 2(R₃Sn)₂O + 2R′NH·CO·X → R₃Sn·NR′·CO·NR′·SnR₃+ 2R₃SnX + CO₂+ H₂O, and primary amido-compounds give the trialkyltin isocyanate according to the equation (R₃Sn)₂O + 2NH₂·CO·X → 2R₃Sn·NCO + 2HX + H₂O. Evidence is presented that both of these more complex reactions involve initial N-trialkylstannylation. Reports in the literature that carboxylic esters react with bistrialkyltin oxides to give ethers, and that trialkyltin isocyanates react with amines to give trialkylstannylureas, could not be confirmed.