Journal of Physical Chemistry p. 4929 - 4932 (1983)
Update date:2022-08-03
Topics:
To, Kar-Chun
Wolf, A. P.
Rack, E. P.
The stereochemistry of translationally energetic fluorine-for-halogen and chlorine-for-halogen substitution was studied in gaseous 2(S)- and 2(R)-halopropionyl halides.While net inversion of configuration was observed for halogen using 34mCl as the displacing agent, predominant retention of configuration was found when 18F was used as the displacing agent on the chiral centers of the 2-halopropionyl halides.The extent of inversion or retention in these energetic substitution reactions appears to be sensitive to the mass of the incoming atom, to steric hindrance to back-side attack, and to the nature of the halogen leaving group.
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