87337-53-9Relevant academic research and scientific papers
Stereochemical Consequences of Halogen-for-Halogen Substitutions in the Gas Phase
To, Kar-Chun,Wolf, A. P.,Rack, E. P.
, p. 4929 - 4932 (1983)
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.
Stereochemical Consequences of Bromine-for-Halogen Substitutions in the Gas Phase
Firouzbakht, Mahmoud L.,Ferrieri, Richard A.,Wolf, Alfred P.,Rack, Edward P.
, p. 5339 - 5343 (2007/10/02)
The stereochemistry of translationally excited bromine-for-halogen substitution was studied in gaseous 2(S)- and 2(R)-halopropionyl halides.Net inversion of configuration was observed for 75Br-for-X substitutions with a trend of increasing inversion as the displaced atom was varied in the series, X = F, Cl, Br.A correlation with previous studies on 18F-for-X and 34mCl-for-X substitutions also showed increased inversion with increased mass of the displacing agent.In addition, these recoil atom substitutions showed an apparent independence from the free-energy requirement of reaction.
