Q. Mir, J. Shreeve
Sep 1, 1994
Citations
0
Influential Citations
10
Citations
Journal
Journal of Fluorine Chemistry
Abstract
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 phenylphosphonothionic chloride give rise to more highly substituted olefins and new macrofluoroheterocycles.