Synthesis of highly-strained gem-difluoro compounds by reaction of difluoromethylene with cycloalkenes

Author

Deyi Yang, New Jersey Institute of Technology

Document Type

Thesis

Date of Award

5-31-1989

Degree Name

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

Department

Chemical Engineering, Chemistry and Environmental Science

First Advisor

Arthur Greenberg

Second Advisor

Barbara B. Kebbekus

Third Advisor

Guanli Wu

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.

Recommended Citation

Yang, Deyi, "Synthesis of highly-strained gem-difluoro compounds by reaction of difluoromethylene with cycloalkenes" (1989). Theses. 1925.
https://digitalcommons.njit.edu/theses/1925