The Unexpected Formation of 9,9,10,10-Tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene

Alex J. Roche, Khalil A. Abboud, William R. Dolbier

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


An investigation of the palladium-catalyzed Kumada cross-coupling reaction between PhMgBr and (pseudo-ortho) 4,12-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane revealed that in addition to the expected cross-coupled product, an unintended major product was generated. The product was determined to be 9,9,10,10-tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene by X-ray crystallography and is proposed to be formed via the first reported example of reductive defluorination by a Grignard reagent. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)5355-5358
Number of pages4
JournalJournal of Organic Chemistry
Issue number10
StatePublished - May 15 2015

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


Dive into the research topics of 'The Unexpected Formation of 9,9,10,10-Tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene'. Together they form a unique fingerprint.

Cite this