Is radical dehalogenation possible?

1 Answer
Dec 23, 2014

Yes, indeed. Radical dehalogenation is an important process in organic synthesis.

The process often involves tributyltin hydride, (C₄H₉)₃SnH.

For example, (C₄H₉)₃SnH undergoes a free radical reaction with 1-bromopropane to produce propane.

CH₃CH₂CH₂Br + (C₄H₉)₃SnH → CH₃CH₂CH₃ + (C₄H₉)₃SnBr

The initiation step involves the formation of the tributyltin free radical, (C₄H₉)₃Sn·.

Then the free radical keeps reacting and being regenerated in the propagation steps.

As usual, there are several termination steps.