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

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 Jr

J Org Chem. 2015 May 15;80(10):5355-8.

PMID: 25897785

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3345297	1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane		3345-29-7	Price

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