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For NHCs with small alkyl substituents at nitrogen (<jats:italic>R<\/jats:italic>=Me, <jats:italic>n<\/jats:italic>Pr, <jats:italic>i<\/jats:italic>Pr) the adducts NHC\u2009\u22c5\u2009PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub> (<jats:bold>2\u2009a<\/jats:bold>\u2013<jats:bold>h<\/jats:bold>) were isolated. The reaction with the sterically more demanding NHCs Dipp<jats:sub>2<\/jats:sub>Im (1,3\u2010bis\u2010(2,6\u2010di\u2010<jats:italic>iso<\/jats:italic>\u2010propylphenyl)\u2010imidazolin\u20102\u2010ylidene) (<jats:bold>1\u2009i<\/jats:bold>) and <jats:italic>t<\/jats:italic>Bu<jats:sub>2<\/jats:sub>Im (1,3\u2010di\u2010<jats:italic>tert<\/jats:italic>\u2010butyl\u2010imidazolin\u20102\u2010ylidene) (<jats:bold>1\u2009j<\/jats:bold>) afforded the <jats:italic>a<\/jats:italic>NHC adducts <jats:bold>3\u2009i<\/jats:bold> and <jats:bold>3\u2009j<\/jats:bold> (<jats:italic>a<\/jats:italic> denotes \u201cabnormal\u201d NHC coordination <jats:italic>via<\/jats:italic> a backbone carbon atom). The use of <jats:italic>t<\/jats:italic>BuMeIm (1\u2010<jats:italic>tert<\/jats:italic>\u2010butyl\u20103\u2010methyl\u2010imidazolin\u20102\u2010ylidene) (<jats:bold>1\u2009m<\/jats:bold>) led to partial decomposition of the NHC and formation of the salt [<jats:italic>t<\/jats:italic>BuMeIm\u2212H][MeIm\u2009\u22c5\u2009PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>] (<jats:bold>4\u2009m<\/jats:bold>). The phosphorane PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub> forms adducts with PMe<jats:sub>3<\/jats:sub> but does not react with PPh<jats:sub>3<\/jats:sub> or PCy<jats:sub>3<\/jats:sub>. The <jats:italic>mer<\/jats:italic>\u2010<jats:italic>cis<\/jats:italic> isomer of literature\u2010known Me<jats:sub>3<\/jats:sub>P\u2009\u22c5\u2009PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub> (<jats:bold>5\u2009a<\/jats:bold>) was structurally characterized. Mixtures of the phosphorane PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub> and the sterically encumbered NHCs <jats:italic>t<\/jats:italic>Bu<jats:sub>2<\/jats:sub>Im, Dipp<jats:sub>2<\/jats:sub>Im, and Dipp<jats:sub>2<\/jats:sub>Im<jats:sup>H2<\/jats:sup> (1,3\u2010bis\u2010(2,6\u2010di\u2010<jats:italic>iso<\/jats:italic>\u2010propylphenyl)\u2010imidazolidin\u20102\u2010ylidene) (<jats:bold>1\u2009k<\/jats:bold>) showed properties of FLPs (Frustrated <jats:italic>Lewis<\/jats:italic> Pairs) as these mixtures were able to open the ring of THF (tetrahydrofuran) to yield NHC\u2212(CH<jats:sub>2<\/jats:sub>)<jats:sub>4<\/jats:sub>O\u2212PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub> <jats:bold>6\u2009i<\/jats:bold>\u2013<jats:bold>k<\/jats:bold>. Furthermore, the deprotonation of the weak C\u2212H acids CH<jats:sub>3<\/jats:sub>CN, acetone, and ethyl acetate was achieved, which led to the formation of the corresponding imidazolium salts and the phosphates [PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>(CH<jats:sub>2<\/jats:sub>CN)]<jats:sup>\u2212<\/jats:sup> (<jats:bold>7<\/jats:bold>), [PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>(OC(=CH<jats:sub>2<\/jats:sub>)CH<jats:sub>3<\/jats:sub>)]<jats:sup>\u2212<\/jats:sup> (<jats:bold>8<\/jats:bold>) and [PF<jats:sub>2<\/jats:sub>(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>(CH<jats:sub>2<\/jats:sub>CO<jats:sub>2<\/jats:sub>Et)]<jats:sup>\u2212<\/jats:sup> (<jats:bold>9<\/jats:bold>).<\/jats:p>","DOI":"10.1002\/ejic.202100183","type":"journal-article","created":{"date-parts":[[2021,3,9]],"date-time":"2021-03-09T03:38:09Z","timestamp":1615261089000},"page":"1941-1960","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Tris(pentafluoroethyl)difluorophosphorane and <i>N<\/i>\u2010Heterocyclic Carbenes: Adduct Formation and Frustrated <i>Lewis<\/i> Pair Reactivity"],"prefix":"10.1002","volume":"2021","author":[{"given":"Steffen A.","family":"F\u00f6hrenbacher","sequence":"first","affiliation":[{"name":"Institute of Inorganic Chemistry Julius-Maximilians-Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}]},{"given":"Vivien","family":"Zeh","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry Julius-Maximilians-Universit\u00e4t W\u00fcrzburg  Am Hubland 97074 W\u00fcrzburg Germany"}]},{"given":"Mirjam 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