Stereospecific mono- and difluorination of the C7-bridge of norbornenes

David E. Rajsfus, Sari Alter-Zilberfarb, Pessia Sharon, Mary Ann B. Meador, Aryeh A. Frimer

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


Fluorinated norbornenes are very desirable monomers in the semiconductor and high-temperature polyimide industries. We describe herein a synthetic strategy for the stereospecific mono- or difluorination of the C 7-carbon in norbornene systems beginning with 7-ketonadic anhydride 1. In particular, anti-7-fluoro methyl diester 4 and its 7,7-difluoronadic analog 7 can be prepared from 1 in 3 or 4 steps: saponification, reduction (for 4), esterification, fluorination with DAST. In addition, anti-7-fluoro-syn-7- fluoromethylnadic diester 16 is obtained from epoxide 14, and dimethyl 7,7-difluorobicyclo[2.2.2]oct-5-ene-2,3-dicarboxylate (17) from ketone 15. Anchimeric assistance of the norbornene double bond guides the introduction of attacking fluoride anions stereospecifically anti to the olefinic linkage.

Original languageEnglish
Pages (from-to)339-347
Number of pages9
JournalJournal of Fluorine Chemistry
Issue number5
StatePublished - May 2011


  • 7,7-Difluoronadic
  • 7-Fluoronadic
  • Anchimeric assistance
  • Diethylaminosulfur trifluoride
  • Stereospecific fluorination


Dive into the research topics of 'Stereospecific mono- and difluorination of the C7-bridge of norbornenes'. Together they form a unique fingerprint.

Cite this