ChemInform Abstract: Stereochemistry and Some Kinetic Aspects of Fluorination of Phenyl- Substituted Alkenes with SelectfluorTM Reagent F-TEDA-BF4

Reactions of phenyl-substituted alkenes with SelectfluorTM fluorinating reagent F-TEDA-BF4 in the presence of various alcohols resulted in the formation of vicinal fluoroalkoxy adducts with Markovnikov type of regioselectivity. The stereochemistry of the fluoro-methoxylation addition reaction was found to be slightly syn predominant in the case of (Z)-stilbene, indene, and dibenzosuberenone, while equal amounts of both diastereoisomers were formed in the case of (E)-1-phenyl-1-propene and acenaphthylene. In the phenyl-substituted benzocyclene series the stereochemistry of fluoro-alkoxylation was found to be dependent on ring size and on the structure of the alcohol. The resulting vicinal fluoroalkoxy adducts were transformed by heating in aqueous HBr to 2-fluoro-1-phenylbenzocyclenes. Correlation of the logarithms of relative rates of fluoro-methoxylation reactions in a series of ten α-phenyl and α,α-diphenyl acyclic and cyclic alkenes with the ionization potentials of these alkenes resulted in a linear r...