{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,2]],"date-time":"2026-05-02T06:40:32Z","timestamp":1777704032987,"version":"3.51.4"},"reference-count":53,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2023,1,31]],"date-time":"2023-01-31T00:00:00Z","timestamp":1675123200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPlusChem"],"published-print":{"date-parts":[[2023,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Phosphoranides comprising three phosphorus carbon bonds are scarcely represented in the literature. We now utilized tris(pentafluoroethyl)phosphane, P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>, and cyanobis(pentafluoroethyl)phosphane, P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(CN), featuring electron withdrawing pentafluoroethyl groups, to synthesize such compounds. Metal fluorides MF (M=Ag, Cs) add to P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub> yielding respective M[P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>F] salts. Those M[P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>F] subsequently suffer a loss of C<jats:sub>2<\/jats:sub>F<jats:sub>4<\/jats:sub>, furnishing M[P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>F<jats:sub>2<\/jats:sub>]. The cesium salt decomposes instantaneously when warmed to rt, whereas the silver salt decomposes slowly over several days at rt. Treatment of Ag[P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>F] with 2,2\u2019\u2010bipyridine facilitated the isolation and structural characterization of [Ag(bipy){P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>F}]. With P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(CN), AgF reacts under substitution of the cyano group yielding P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>F, rather than phosphoranide formation. However, [K(18\u2010crown\u20106)]F adds to P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(CN) furnishing [K(18\u2010crown\u20106)][P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(CN)F]. Its structural characterization was successful, despite its tendency to undergo an exchange of substituents, yielding [K(18\u2010crown\u20106)][P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>F<jats:sub>2<\/jats:sub>] and presumably [K(18\u2010crown\u20106)][P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(CN)<jats:sub>2<\/jats:sub>]. The latter forms an equilibrium with [K(18\u2010crown\u20106)]CN and P(C<jats:sub>2<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(CN) which lies well on side of the phosphane and cyanide salt.<\/jats:p>","DOI":"10.1002\/cplu.202200436","type":"journal-article","created":{"date-parts":[[2023,1,17]],"date-time":"2023-01-17T11:00:19Z","timestamp":1673953219000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Triorganylphosphoranides: Realization of an Unusual Structural Motif Utilizing Electron Withdrawing Pentafluoroethyl Groups"],"prefix":"10.1002","volume":"88","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2242-239X","authenticated-orcid":false,"given":"Mira","family":"Ke\u00dfler","sequence":"first","affiliation":[{"name":"Centrum f\u00fcr Molekulare Materialien Universit\u00e4t Bielefeld  Universit\u00e4tsstra\u00dfe 25 33615 Bielefeld Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6008-4961","authenticated-orcid":false,"given":"Michael","family":"Kapiza","sequence":"additional","affiliation":[{"name":"Centrum f\u00fcr Molekulare Materialien Universit\u00e4t Bielefeld  Universit\u00e4tsstra\u00dfe 25 33615 Bielefeld Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hans\u2010Georg","family":"Stammler","sequence":"additional","affiliation":[{"name":"Centrum f\u00fcr Molekulare Materialien Universit\u00e4t Bielefeld  Universit\u00e4tsstra\u00dfe 25 33615 Bielefeld Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Beate","family":"Neumann","sequence":"additional","affiliation":[{"name":"Centrum f\u00fcr Molekulare Materialien Universit\u00e4t Bielefeld  Universit\u00e4tsstra\u00dfe 25 33615 Bielefeld Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gerd\u2010Volker","family":"R\u00f6schenthaler","sequence":"additional","affiliation":[{"name":"Department of Life Sciences and Chemistry Jacobs University Bremen  Campus Ring 1 28759 Bremen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9610-8478","authenticated-orcid":false,"given":"Berthold","family":"Hoge","sequence":"additional","affiliation":[{"name":"Centrum f\u00fcr Molekulare Materialien Universit\u00e4t Bielefeld  Universit\u00e4tsstra\u00dfe 25 33615 Bielefeld Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,1,31]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"crossref","unstructured":"G. M\u00fcller H.-J. Matheus M. Winkler Z. Naturforsch.2001 56 b 1155;","DOI":"10.1515\/znb-2001-1110"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja807828t"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic801833a"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2SC21214E"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404628"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201308309"},{"key":"e_1_2_8_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201308309"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC02423D"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.201800264"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00029a011"},{"key":"e_1_2_8_11_1","unstructured":"\u00a0"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00491a062"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00510a030"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19831161005"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39850000562"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1080\/03086648708080552"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00290a023"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00266-F"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9910614"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.08.004"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00395a049"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426509408037442"},{"key":"e_1_2_8_23_1","first-page":"435","volume-title":"ACS Symposium Series: Phosphorus Chemistry","author":"Granoth I.","year":"1981"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197904112"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19790910524"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197909351"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19790911209"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/DT9810000413"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19824880102"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/dt9900000551"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/dt9900002593"},{"key":"e_1_2_8_30_1","unstructured":"\u00a0"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1080\/10426509608545224"},{"key":"e_1_2_8_32_2","unstructured":"O. Shyshkov Dissertation Universit\u00e4t Bremen Bremen 2006."},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202104308"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2014.10.007"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.1c02307"},{"key":"e_1_2_8_36_1","unstructured":"\u00a0"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.202000047"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.202000198"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.2c01143"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201402421"},{"key":"e_1_2_8_41_1","volume-title":"gNMR","author":"Budzelaar P. H. M.","year":"2006"},{"key":"e_1_2_8_42_1","first-page":"1349","volume-title":"J. Chem. Soc., Dalton Trans.","author":"Addison A. W.","year":"1984"},{"key":"e_1_2_8_43_1","volume-title":"Methods in stereochemical analysis, Vol. 8","author":"Verkade J. G.","year":"1987"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic800611h"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00086a018"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889808042726"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024218"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053273314026370"},{"key":"e_1_2_8_49_1","unstructured":"U. Welz-Biermann N. Ignatyev M. Weiden M. Schmidt U. Heider A. Miller H. Willner P. Sartori WO2003-EP2739 2003."},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1071\/CH9720493"}],"container-title":["ChemPlusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cplu.202200436","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cplu.202200436","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cplu.202200436","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T20:31:40Z","timestamp":1760387500000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cplu.202200436"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,31]]},"references-count":53,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2023,7]]}},"alternative-id":["10.1002\/cplu.202200436"],"URL":"https:\/\/doi.org\/10.1002\/cplu.202200436","archive":["Portico"],"relation":{},"ISSN":["2192-6506","2192-6506"],"issn-type":[{"value":"2192-6506","type":"print"},{"value":"2192-6506","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,31]]},"assertion":[{"value":"2022-12-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-01-31","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202200436"}}