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The cation was prepared <jats:italic>via<\/jats:italic> methoxide ion abstraction of an alkynyl phosphine <jats:bold>1<\/jats:bold>. Electron rich <jats:italic>N<\/jats:italic>\u2010heterocyclic imine substituents and a \u03c0 conjugated fluorenyl scaffold together stabilize the resulting three\u2010coordinate phosphonium center of [<jats:bold>2<\/jats:bold>]<jats:sup>+<\/jats:sup>. [<jats:bold>2<\/jats:bold>]<jats:sup>+<\/jats:sup> features a trigonal planar phosphorus atom which is electrophilic, as evidenced experimentally by the preparation of a Lewis acid\u2010base adduct with 4\u2010dimethylaminopyridine, and fluoride ion affinity calculations. Crystallographic and computational investigations of [<jats:bold>2<\/jats:bold>]<jats:sup>+<\/jats:sup> support a structure with considerable P\u2550C double bond character. Furthermore, this P\u2550C double bond participates in a thermally reversible intramolecular dearomative [2\u00a0+\u00a02] cycloaddition with an arene moiety of one of its supporting 1,3\u2010diisopropylphenylimidazolin\u20102\u2010ylidenamino substituents to give a tetracyclic isomer [<jats:bold>2<jats:sup>cyclo<\/jats:sup><\/jats:bold>]<jats:sup>+<\/jats:sup>. The isolation of a free [R<jats:sub>2<\/jats:sub>P\u2550C\u2550C\u2550CAr<jats:sub>2<\/jats:sub>]<jats:sup>+<\/jats:sup> draws further parallels between the properties and reactivity of low\u2010coordinate phosphorus compounds and related carbon compounds.<\/jats:p>","DOI":"10.1002\/anie.202502201","type":"journal-article","created":{"date-parts":[[2025,3,13]],"date-time":"2025-03-13T12:44:57Z","timestamp":1741869897000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Allenylidene Phosphonium Ion: An Isoelectronic Phosphorus Analogue of [3]Cumulene"],"prefix":"10.1002","volume":"64","author":[{"given":"Lucas C.","family":"Torres","sequence":"first","affiliation":[{"name":"Department of Chemistry York University  4700 Keele St Toronto ON M3J 1P3 Canada"},{"name":"Institute of General, Inorganic and Theoretical Chemistry Universit\u00e4t Innsbruck  Innrain 80\u201382 Innsbruck 6020 Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pawel","family":"L\u00f6we","sequence":"additional","affiliation":[{"name":"Institute of Inorganic and Analytical Chemistry Westf\u00e4lische Wilhelms\u2010Universit\u00e4t M\u00fcnster  48149, Corrensstrasse 30 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Avik","family":"Bhattacharjee","sequence":"additional","affiliation":[{"name":"Department of Chemistry York University  4700 Keele St Toronto ON M3J 1P3 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maike B.","family":"R\u00f6thel","sequence":"additional","affiliation":[{"name":"Institute of General, Inorganic and Theoretical Chemistry Universit\u00e4t Innsbruck  Innrain 80\u201382 Innsbruck 6020 Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Seidl","sequence":"additional","affiliation":[{"name":"Institute of General, Inorganic and Theoretical Chemistry Universit\u00e4t Innsbruck  Innrain 80\u201382 Innsbruck 6020 Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jesse","family":"LeBlanc","sequence":"additional","affiliation":[{"name":"Department of Chemistry York University  4700 Keele St Toronto ON M3J 1P3 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Klaus","family":"Wurst","sequence":"additional","affiliation":[{"name":"Institute of General, Inorganic and Theoretical Chemistry Universit\u00e4t Innsbruck  Innrain 80\u201382 Innsbruck 6020 Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fabian","family":"Dielmann","sequence":"additional","affiliation":[{"name":"Institute of General, Inorganic and Theoretical Chemistry Universit\u00e4t Innsbruck  Innrain 80\u201382 Innsbruck 6020 Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher B.","family":"Caputo","sequence":"additional","affiliation":[{"name":"Department of Chemistry York University  4700 Keele St Toronto ON M3J 1P3 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,4,10]]},"reference":[{"key":"e_1_2_9_1_1","volume-title":"Phosphorus; The Carbon Copy","author":"Dillon K. 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