The extent to which Sn-CH2 and/or Sn-CH3 cleavage occurs in (CH3) 3SnCH2M (CH3) 3 (M= Sn, Ge, Si) in reactions with several electrophiles has been determined. With iodine and with bromine in various solvents both sites are attacked with Sn-CH2 cleavage favored for nonpolar solvents and for M= Sn. Protolysis leads to Sn-CH2 cleavage only, and this site appears to be activated by the (CH3) 3M groups. On the other hand organometallic ...