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

Abstract

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
Volume80
Issue number10
DOIs
StatePublished - May 15 2015

ASJC Scopus subject areas

  • Organic Chemistry

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