This research report discusses the reactions of CF2Br2 with various alkenes. Attempts to synthesize some gemdifluorocyclopropanes from alkenes and CF2x2 (X=Br, I) by modified Simmons-Smith procedures were Dehydrohalogenation reactions of some not successful. 1,3-dibromo-1,1- difluoroalkanes were conducted with potassium hydroxide or tributylamine. Heating cis or trans 1-(bromodifluoromethyl)- 2-bromocyclohexane with potassium hydroxide does not produce the expected gem-difluorodienes but instead gives the corresponding a,$ -unsaturated carboxylic acid. The mechanism for the productions of the various reaction intermediates from the reaction of the cyclic dibromide with potassium hydoxide is proposed. Experimental evidence supporting the proposed mechanism is presented. Gemdifluorodienes are isolated when the base tributylamine is used. 1H NMR, 13c NMR and IR spectral data are presented and interpretations are also included.
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Master of Science (M.S.)
College of Arts and Sciences
Length of Campus-only Access
Masters Thesis (Open Access)
Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences
Michael, Mariana, "Unexpected products from the reactions of 1-(bromodifluoromethyl)-2-(bromoalkanes with potassium hydroxide,characterization of some gen-difluorodienes and attempted syntheses of gem-difluorocyclopropanes" (1988). Retrospective Theses and Dissertations. 4312.