The New Jersey Institute of Technology's
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Title:	Synthesis of highly-strained gem-difluoro compounds by reaction of difluoromethylene with cycloalkenes
Author:	Yang, Deyi
View Online:	njit-etd1989-059 (iv, 48 pages ~ 1.2 MB pdf)
Department:	Department of Chemical Engineering, Chemistry and Environmental Science
Degree:	Master of Science
Program:	Chemistry
Document Type:	Thesis
Advisory Committee:	Greenberg, Arthur (Committee chair) Kebbekus, Barbara B. (Committee member) Wu, Guanli (Committee member)
Date:	1989-05
Keywords:	Organofluorine compounds -- Synthesis Chemistry, Organic -- Synthesis
Availability:	Unrestricted
Abstract:	Trans-Cyclooctene is thought to be more reactive than cis-cyclooctene due to its trans-structure. When cis or trans-clooctene reacts with difluormethylene (:CF2), trans-9,9-difluorobicyclo[ 6,1,0] nonane was generated in much higher yield than cis-9,9-difluorobicyclo[6,1,0]nonane. [PhCF3P+CF2Br]Br- was chosen to be the difluoromethylene precursor in this study. The reason was that the reaction condition for trans-cyclooctene and :CF2 should be at low temperature. Only [PhCF3P+CF2Br]Br- could generate CF2 at lower temperature (e.g. room temperature). We succeeded in the synthesis of trans-9,9-difluorobicyclo[6,1,0]nonane and its cis isomer and have demonstrated a principle of CF2 reactivity.