Reactions involving fluoride ion. Part 27. Reactions of perfluoro-3,4-dimethylhex-3-ene with carbon nucleophiles
Abstract
Reaction of methyl- and ethyl-lithium with perfluoro-3,4-dimethylhex-3-ene (1) gives products arising from nucleophilic attack with allylic displacement of fluorine from both CF3 and CF2 positions. Phenylmagnesium bromide gives biphenyl via a process which appears to involve one-electron transfer to (1). Enolate anions undergo substitution in (1) with concomitant cyclisation to give fluorinated pyran derivatives.