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The pentafluorosulfanyl functional group, -SF5, also known the sulfur pentafluoride group, is a strong electron withdrawing group, which is stable under a variety of harsh conditions. Its presence on a molecule confers increased lipophilicity. The sulfur has octahedral geometry around it.
Properties
editSlightly smaller than a tert-butyl group, larger than a trifluoromethyl group. Octahedral geometry around sulfur. Strongly electron withdrawing. Confers increased lipophilicy to molecules
Synthesis
editRadical addition of SF5X compounds, typically SF5Cl or SF5Br, to unsaturated compounds. Addition reactions involving SF5Cl or SF5Br can be catalysed by triethylborane.
Fluorination of suitable sulfur containing precursors. (Using chorine and alkali metal fluorides) need to check.
As of July 2017, there are no commercial applications of any molecules containing the pentafluorosulfanyl group. However there is pentafluorosulfanyl group is promising from the point of view of the development of new drugs and other bioactive molecules due to its unusual combination of properties of high polarity and high lipophilicity.
Materials science
Liquid crystals
temp
editSometimes called pentafluorosulfur or sulfur pentafluoride group.
Sometimes called a super-trifluoromethyl group due to increased electronegativity, lipophilicity, and chemical stablity, as compared to the trifluoromethyl group
some possibly useful references
editReferences
edit- ^ Kanishchev, Oleksandr S.; Dolbier, William R. (2016-01-01). "SF5-Substituted Aromatic Heterocycles". Advances in Heterocyclic Chemistry. Heterocyclic Chemistry in the 21st Century. 120: 1–42. doi:10.1016/bs.aihch.2016.03.008.
- ^ Savoie, Paul R.; Welch, John T. (2015-01-28). "Preparation and Utility of Organic Pentafluorosulfanyl-Containing Compounds". Chemical Reviews. 115 (2): 1130–1190. doi:10.1021/cr500336u. ISSN 0009-2665.
- ^ Kirsch, Peer; Röschenthaler, Gerd-Volker (2007-01-11). Current Fluoroorganic Chemistry. ACS Symposium Series. Vol. 949. American Chemical Society. pp. 221–243. doi:10.1021/bk-2007-0949.ch013. ISBN 0841274037.
- ^ Verma, R. D.; Kirchmeier, Robert L.; Shreeve, Jean'ne M. (1994-01-01). "Chemistry of Pentafluorosulfanyl Compounds". Advances in Inorganic Chemistry. 41: 125–169. doi:10.1016/s0898-8838(08)60171-3.
- ^ Sowaileh, Munia F.; Hazlitt, Robert A.; Colby, David A. (2017-09-21). "Application of the Pentafluorosulfanyl Group as a Bioisosteric Replacement". ChemMedChem. 12 (18): 1481–1490. doi:10.1002/cmdc.201700356. ISSN 1860-7187.
- ^ Altomonte, Stefano; Zanda, Matteo (2012-11-01). "Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules". Journal of Fluorine Chemistry. Special Issue: 2012 ACS Award Issue “For Creative Work in Fluorine Chemistry” David O’Hagan. 143: 57–93. doi:10.1016/j.jfluchem.2012.06.030.