Journal of Fluorine Chemistry p. 269 - 276 (1994)
Update date:2022-08-04
Topics:
Mir, Qui-Chee
Shreeve, Jean'ne M.
1,2-Dichlorohexafluorocyclopent-1-ene and 1,2-dichlorotetrafluorocyclobut-1-ene in tetrahydrofuran solutions of 2-mercaptoethanol or 1,2-ethanedithiol and triethylamine give new mono- or di-substituted cycloolefins by displacement of one or two of the chlorine atoms at the double bond by -SCH2CH2OH or -SCH2CH2SH groups, respectively, as a function of the stoichiometry of the reactions.In several cases, the formation of spirocyclic compounds result via an intramolecular cyclization process with concomitant double-bond shift and loss of fluoride ion.Reactions of the spirocycles with nucleophiles, such as N-methylpiperazine, perfluoroglutaryl fluoride and phenylphosphonotionic chloride give rise to more highly substituted olefins and new macrofluoroheterocycles.
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