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Synthesis and Elaboration of All‐ cis ‐1,2,4,5‐Tetrafluoro‐3‐Phenylcyclohexane: A Polar Cyclohexane Motif
Author(s) -
Durie Alastair J.,
Fujiwara Tomoya,
Cormanich Rodrigo,
Bühl Michael,
Slawin Alexandra M. Z.,
O'Hagan David
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400354
Subject(s) - elaboration , cyclohexane , motif (music) , polar , chemistry , stereochemistry , organic chemistry , physics , philosophy , aesthetics , astronomy , humanities
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 CF 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 J HF and 2h J CF 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.