{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,19]],"date-time":"2026-09-19T01:17:23Z","timestamp":1789780643730,"version":"4.0.1"},"reference-count":94,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2016,11,30]],"date-time":"2016-11-30T00:00:00Z","timestamp":1480464000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2017,1,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Two [3+1] fragmentations of the Lewis acid stabilized bicyclo[1.1.0]tetraphosphabutanide Li[Mes*P<jats:sub>4<\/jats:sub>\u22c5 BPh<jats:sub>3<\/jats:sub>] (Mes*=2,4,6\u2010tBu<jats:sub>3<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>2<\/jats:sub>) are reported. The reactions proceed by extrusion of a P<jats:sub>1<\/jats:sub> fragment, induced by either an imidazolium salt or phenylisocyanate, with release of the transient triphosphirene Mes*P<jats:sub>3<\/jats:sub>, which was isolated as a dimer and trapped by 1,3\u2010cyclohexadiene as a Diels\u2013Alder adduct. DFT quantum chemical computations were used to delineate the reaction mechanisms. These unprecedented pathways grant access to both P<jats:sub>1<\/jats:sub>\u2010 and P<jats:sub>3<\/jats:sub>\u2010containing organophosphorus compounds in two simple steps from white phosphorus.<\/jats:p>","DOI":"10.1002\/anie.201607234","type":"journal-article","created":{"date-parts":[[2016,11,30]],"date-time":"2016-11-30T09:43:17Z","timestamp":1480498997000},"page":"285-290","source":"Crossref","is-referenced-by-count":35,"title":["Selective [3+1] Fragmentations of P<sub>4<\/sub> by \u201cP\u201d Transfer from a Lewis Acid Stabilized [RP<sub>4<\/sub>]<sup>\u2212<\/sup> Butterfly Anion"],"prefix":"10.1002","volume":"56","author":[{"given":"Jaap E.","family":"Borger","sequence":"first","affiliation":[{"name":"Department of Chemistry and Pharmaceutical Sciences Vrije Universiteit Amsterdam  De Boelelaan 1083 1081 HV Amsterdam The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andreas W.","family":"Ehlers","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Pharmaceutical Sciences Vrije Universiteit Amsterdam  De Boelelaan 1083 1081 HV Amsterdam The Netherlands"},{"name":"Department of Chemistry University of Johannesburg  Auckland Park Johannesburg 2006 South Africa"},{"name":"Van 't Hoff Institute for Molecular Sciences University of Amsterdam  Science Park 904 1098 XH Amsterdam The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Lutz","sequence":"additional","affiliation":[{"name":"Crystal and Structural Chemistry, Bijvoet Center for Biomolecular Research Utrecht University  Padualaan 8 3584 CH Utrecht The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J. Chris","family":"Slootweg","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Pharmaceutical Sciences Vrije Universiteit Amsterdam  De Boelelaan 1083 1081 HV Amsterdam The Netherlands"},{"name":"Van 't Hoff Institute for Molecular Sciences University of Amsterdam  Science Park 904 1098 XH Amsterdam The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Koop","family":"Lammertsma","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Pharmaceutical Sciences Vrije Universiteit Amsterdam  De Boelelaan 1083 1081 HV Amsterdam The Netherlands"},{"name":"Department of Chemistry University of Johannesburg  Auckland Park Johannesburg 2006 South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,11,30]]},"reference":[{"key":"e_1_2_2_1_1","volume-title":"Phosphorus 2000","author":"Corbridge D. E. C.","year":"2000"},{"key":"e_1_2_2_2_1","unstructured":"For reviews 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other examples of P4-derived bicyclo[1.1.0]tetraphosphabutane derivatives 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two cationic examples prepared from P1building blocks see:"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201109010"},{"key":"e_1_2_2_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201109010"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500892"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500892"},{"key":"e_1_2_2_47_1","unstructured":"The anion has never been isolated but was detected by31P\u2005NMR spectroscopy by Baudler et\u2005al. who after the reduction of P4with Na\/K naphthalenide observed [HP4]\u2212at low temperature; [HP4]\u2212was also recently detected by M\u00e9zailles and co-workers by the use of borohydrides:"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198810591"},{"key":"e_1_2_2_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881000817"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC01683A"},{"key":"e_1_2_2_50_1","unstructured":"\u00a0"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405879"},{"key":"e_1_2_2_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201405879"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508916"},{"key":"e_1_2_2_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201508916"},{"key":"e_1_2_2_53_1","unstructured":"Note that the reaction of1\u2009awith the metal carbonyl complex [(MeCN)W(CO)5] affords anionic Li[Mes*P4\u22c5(W(CO)5)2] (see Ref.\u2005[13b])."},{"key":"e_1_2_2_54_1","unstructured":"Spectral parameters were determined by iterative full line-shape analysis by using the gNMR simulation program: P.\u2005H.\u2005M. Budzelaar gNMR version\u20055.0.6.0 2006."},{"key":"e_1_2_2_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja077296u"},{"key":"e_1_2_2_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja4072699"},{"key":"e_1_2_2_57_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3SC53140F"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201501017"},{"key":"e_1_2_2_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408354"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201408354"},{"key":"e_1_2_2_59_1","unstructured":"IDipp\u2212BPh3can be considered as a quenched frustrated Lewis pair (FLP) in equilibrium with its constituents."},{"key":"e_1_2_2_60_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802705"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200802705"},{"key":"e_1_2_2_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503808"},{"key":"e_1_2_2_62_1","unstructured":"CCDC\u20051491988 1491989 and 1491990contain the supplementary crystallographic data for this paper. These data can be obtained free of charge fromThe Cambridge Crystallographic Data Centre."},{"key":"e_1_2_2_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC00963D"},{"key":"e_1_2_2_64_1","unstructured":"Complexes9\u2032and11\u2032feature a PhNCO\u22c5\u22c5\u22c5Li+interaction the energy of which is overestimated and is moderated in solution by the coordination of THF solvent molecules to the Li+cation."},{"key":"e_1_2_2_65_1","unstructured":"The addition reactions are templated by the Li+cation."},{"key":"e_1_2_2_66_1","unstructured":"A similar diphosphene intermediate was proposed by Weigand for the NHC-induced [3+2] fragmentation of an [RP5Cl]+cage cation (see Ref.\u2005[3c]) and by Bertrand for the reaction of P4with cyclic (alkyl)(amino)carbenes (CAACs; see Ref.\u2005[4])."},{"key":"e_1_2_2_67_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200906633"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200906633"},{"key":"e_1_2_2_68_1","unstructured":"This selectivity was also observed by Cossairt and Cummins:"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200803971"},{"key":"e_1_2_2_69_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200803971"},{"key":"e_1_2_2_70_2","unstructured":"Ref.\u2005[28]."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201607234","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201607234","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,24]],"date-time":"2023-09-24T14:17:02Z","timestamp":1695565022000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201607234"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,11,30]]},"references-count":94,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2017,1,2]]}},"alternative-id":["10.1002\/anie.201607234"],"URL":"https:\/\/doi.org\/10.1002\/anie.201607234","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,11,30]]}}}