Ready oxidative addition of an alkyl or aryl halide to a tin(II) alkyl or amide; evidence for a free-radical pathway
Abstract
The addition of an alkyl or phenyl halide RX to Sn[CH(SiMe3)2]2(X = Cl, Br, or I) or Sn[N(SiMe3)2]2(X = Br or I) in n-hexane at 20 °C readily affords the 1 : 1-adducts (or 1:2-adduct for RX = CH2Br2 or CH2I2) which shows two sets of diastereotopically distinct Me3Si3 groups for Sn[CH(SiMe3)2]2(X)R but not the nitrogen analogue; optical-activity and e.s.r data suggest a free-radical mechanism with ·SnY2(X) and R· as intermediatesd [Y =(Me3Si)2CH or (Me3Si)2N].
- This article is part of the themed collection: Philip Power at 65: an icon of organometallic chemistry