Document Type


Date of Award


Degree Name

Master of Science in Chemistry - (M.S.)


Chemical Engineering, Chemistry and Environmental Science

First Advisor

Arthur Greenberg

Second Advisor

Barbara B. Kebbekus

Third Advisor

Guanli Wu


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.

Included in

Chemistry Commons



To view the content in your browser, please download Adobe Reader or, alternately,
you may Download the file to your hard drive.

NOTE: The latest versions of Adobe Reader do not support viewing PDF files within Firefox on Mac OS and if you are using a modern (Intel) Mac, there is no official plugin for viewing PDF files within the browser window.