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The First Synthesis and Characterization of Both Diastereomers of a di[2.2]paracyclophane: 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

The First Synthesis and Characterization of Both Diastereomers of a di[2.2]paracyclophane: 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

A J Roche, J X Duan, W R Dolbier Jr, K A Abboud

J Org Chem. 2001 Oct 19;66(21):7055-8.

PMID: 11597229

Abstract:

The synthesis and characterization of both diastereomers of a system comprised of two [2.2]paracyclophane units linked through a single 4,4' bond are described. Both the meso and d,l diastereomers of 4,4'-bis(octafluoro[2.2]paracyclophane) have been prepared via a palladium-catalyzed reductive homocoupling reaction by copper, producing a 3:2 ratio of meso and d,l diastereomers. A similar reductive homocoupling of pseudo-o-iodotrifluoromethyloctafluoro[2.2]paracyclophane gave only the analogous meso diastereomer. Single-crystal X-ray structures were obtained for all of the diparacyclophane products.

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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