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Janus face all-cis 1,2,4,5-tetrakis(trifluoromethyl)- and all-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)- cyclohexanes
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dc.contributor.author | Yu, Cihang | |
dc.contributor.author | Kütt, Agnes | |
dc.contributor.author | Röschenthaler, Gerd-Volker | |
dc.contributor.author | Lebl, Tomas | |
dc.contributor.author | Cordes, David B. | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Buehl, Michael | |
dc.contributor.author | O'Hagan, David | |
dc.date.accessioned | 2020-11-13T09:30:05Z | |
dc.date.available | 2020-11-13T09:30:05Z | |
dc.date.issued | 2020-10-26 | |
dc.identifier | 269274158 | |
dc.identifier | b39e5a2e-7612-4c18-9963-dc8b3720bb9a | |
dc.identifier | 85090058738 | |
dc.identifier | 000564434400001 | |
dc.identifier.citation | Yu , C , Kütt , A , Röschenthaler , G-V , Lebl , T , Cordes , D B , Slawin , A M Z , Buehl , M & O'Hagan , D 2020 , ' Janus face all- cis 1,2,4,5-tetrakis(trifluoromethyl)- and all- cis 1,2,3,4,5,6-hexakis(trifluoromethyl)- cyclohexanes ' , Angewandte Chemie International Edition , vol. 59 , no. 45 , pp. 19905-19909 . https://doi.org/10.1002/anie.202008662 | en |
dc.identifier.issn | 1433-7851 | |
dc.identifier.other | RIS: urn:E304C0A09AD8144559065E07F8A97B2F | |
dc.identifier.other | ORCID: /0000-0002-0269-3221/work/79917784 | |
dc.identifier.other | ORCID: /0000-0002-1095-7143/work/79917822 | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/79917827 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/79917833 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/79917848 | |
dc.identifier.uri | https://hdl.handle.net/10023/20964 | |
dc.description | Authors thank the Engineering and Physical Sciences Research Council (EPSRC) for funding and the Chinese Scholarship Council for a studentship (CY). | en |
dc.description.abstract | We report the synthesis of all‐cis 1,2,4,5‐tetrakis (trifluoromethyl)‐ and all‐cis 1,2,3,4,5,6‐hexakis (trifluoromethyl)‐ cyclohexanes by direct hydrogenation of precursor tetrakis‐ or hexakis‐ (trifluoromethyl)benzenes. The resultant cyclohexanes have a stereochemistry such that all the CF3 groups are on the same face of the cyclohexyl ring. All‐cis 1,2,3,4,5,6‐hexakis(trifluoromethyl)cyclohexane is the most sterically demanding of the all‐cis hexakis substituted cyclohexanes prepared to date, with a barrier (ΔG) to ring inversion calculated at 27 kcal mol−1. The X‐ray structure of all‐cis 1,2,3,4,5,6‐hexakis(trifluoromethyl)cyclohexane displays a flattened chair conformation and the electrostatic profile of this compound reveals a large diffuse negative density on the fluorine face and a focused positive density on the hydrogen face. The electropositive hydrogen face can co‐ordinate chloride (K≈103) and to a lesser extent fluoride and iodide ions. Dehydrofluorination promoted decomposition occurs with fluoride ion acting as a base. | |
dc.format.extent | 5 | |
dc.format.extent | 1400499 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Janus face | en |
dc.subject | Cyclohexanes | en |
dc.subject | Trifluoromethyl groups | en |
dc.subject | Aryl hydrogenation | en |
dc.subject | Triaxial orientations | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | BDC | en |
dc.subject | R2C | en |
dc.subject.lcc | QD | en |
dc.title | Janus face all-cis 1,2,4,5-tetrakis(trifluoromethyl)- and all-cis 1,2,3,4,5,6-hexakis(trifluoromethyl)- cyclohexanes | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | https://doi.org/10.1002/anie.202008662 | |
dc.description.status | Peer reviewed | en |
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