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Synthesis and Elaboration of all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane: A Polar Cyclohexane Motif

Synthesis and Elaboration of all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane: A Polar Cyclohexane Motif

Alastair J Durie, Tomoya Fujiwara, Rodrigo Cormanich, Michael Bühl, Alexandra M Z Slawin, David O'Hagan

Chemistry. 2014 May 19;20(21):6259-63.

PMID: 24740763

Abstract:

A stereocontrolled synthesis of all-cis-1,2,4,5- tetrafluoro-3-phenylcyclohexane is developed as the first functionalised example of this polar cyclohexane motif. The dipolar nature of the ring, arising due to two 1,3-diaxial C-F bonds, is revealed in the solid-state (X-ray) structure. The orthogonal conformation of the aryl and cyclohexyl rings in all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane, and in an ortho-nitro derivative, result in intramolecular (1h)JHF and (2h)JCF NMR couplings relayed through hydrogen bonding. The aryl group of all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane is elaborated in different ways to demonstrate the versatility of this compound for delivering the motif to a range of molecular building blocks.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP827521	Phenylcyclohexane		827-52-1	Price

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