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dc.contributor.authorO'Hagan, David
dc.identifier.citationO'Hagan , D 2020 , ' Polar organofluorine substituents : multivicinal fluorines on alkyl chains and alicyclic rings ' , Chemistry - A European Journal , vol. Early View .
dc.identifier.otherPURE: 266581891
dc.identifier.otherPURE UUID: f816f119-7a34-4b7e-9569-b3bb460a66c9
dc.identifier.otherRIS: urn:08A04456A10667F9386F3236EEE9323A
dc.identifier.otherWOS: 000530883200001
dc.identifier.otherScopus: 85085083898
dc.description.abstractThis review outlines the progression, primarily of our own work, but with important contributions from other labs, on the synthesis and properties of multiple vicinally fluorinated alkyl chains and rings. Chain conformations of individual diastereoisomers with –CHF‐ at adjacent carbons are influenced by stereoelectronic factors associated with the polar C‐F bond and the polarised geminal hydrogens. Generally the chain will prefer a conformation which acts to minimise overall molecular polarity, and where the C‐F bonds orient away from each other. However when vicinal fluorines are positioned on a ring then conformations are more constrained. The ring will adopt optimal conformations such as a chair in cyclohexane and then C‐F bonds can be introduced with a stereochemistry that forces parallel (axial) orientations. In the case of cyclohexane, 1,3‐diaxial arrangements of C‐F bonds impart considerable polarity to the ring, resulting in an electronegative ‘fluorine face’ and an electropositive ‘hydrogen face’. For all‐ syn 1,2,3,4,5,6‐hexafluorocyclohexane, this arrangement generates an unusually polar aliphatic ring system. Most recently the concept has been extended to the preparation of all‐ syn 1,2,3‐trifluorocyclopropanes, a rigid ring system with fluorines on one face and hydrogens on the other. Log Ps of such compounds indicate that they are significantly more polar than their parent alicyclic hydrocarbons and give some positive indication for a future role of such substituents in medicinal chemistry. Expanding to such a role will require access to improved synthesis methods to these motifs and consequently access to a broader a range of building blocks, however some exciting new methods have emerged recently and these are briefly reviewed.
dc.relation.ispartofChemistry - A European Journalen
dc.rightsCopyright © 2020 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at
dc.subjectOrganofluorine chemistryen
dc.subjectSelective fluorinationen
dc.subjectAliphatic conformationen
dc.subjectAlicyclic chemistryen
dc.subjectQD Chemistryen
dc.titlePolar organofluorine substituents : multivicinal fluorines on alkyl chains and alicyclic ringsen
dc.typeJournal itemen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.description.statusPeer revieweden

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