Stereochemistry of the SE2 Bromine Cleavage of Tetraalkyltin Compounds in Carbon Tetrachloride and Methanol Solvents

  • Richard L. Chambers
  • Frederick R. Jensen


It was demonstrated previously that the SE2 cleavage of sec-Bu*Sn(neopentyl)3 by bromine in methanol occurs with inversion of configuration; this inversion has now been found to be quantitative. It is shown, and explanations are offered for the phenomenon, that cleavage in carbon tetrachloride as solvent (with necessary inhibitors for the concomitant free radical reactions) occurs with retention of configuration. The reversal of stereochemistry may result, not from change in mechanism, but rather from drastic changes in the rate of competing reactions with change of solvent.


Carbon Tetrachloride Organotin Compound Force Retention Bromine Radical Inversion Mechanism 
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Copyright information

© Plenum Press, New York 1978

Authors and Affiliations

  • Richard L. Chambers
    • 1
  • Frederick R. Jensen
    • 1
  1. 1.Department of ChemistryUniversity of CaliforniaBerkeleyUSA

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