{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T22:29:17Z","timestamp":1791930557344,"version":"4.3.4"},"reference-count":66,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2015,11,27]],"date-time":"2015-11-27T00:00:00Z","timestamp":1448582400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Netherlands Organization for Scientific Research"},{"name":"NWO\/CW"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2016,1,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The transient bicyclo[1.1.0]tetraphosphabutane anion, generated from white phosphorus (P<jats:sub>4<\/jats:sub>) and Mes*Li (Mes*=2,4,6\u2010tBu<jats:sub>3<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>2<\/jats:sub>), can be trapped by BPh<jats:sub>3<\/jats:sub> in THF. This Lewis acid stabilized anion can be used as an [RP<jats:sub>4<\/jats:sub>]<jats:sup>\u2212<\/jats:sup> transfer agent, reacting cleanly with neutral Lewis acids (B(C<jats:sub>6<\/jats:sub>F<jats:sub>5<\/jats:sub>)<jats:sub>3<\/jats:sub>, BH<jats:sub>3<\/jats:sub>, and W(CO)<jats:sub>5<\/jats:sub>) to afford unique singly and doubly coordinated butterfly anions, and with the trityl cation to form a neutral, nonsymmetrical, all\u2010carbon\u2010substituted P<jats:sub>4<\/jats:sub>\u2005derivative. This reaction path enables a simple, stepwise functionalization of white phosphorus.<\/jats:p>","DOI":"10.1002\/anie.201508916","type":"journal-article","created":{"date-parts":[[2015,11,27]],"date-time":"2015-11-27T11:26:46Z","timestamp":1448623606000},"page":"613-617","source":"Crossref","is-referenced-by-count":49,"title":["Stabilization and Transfer of the Transient [Mes*P<sub>4<\/sub>]<sup>\u2212<\/sup> Butterfly Anion Using BPh<sub>3<\/sub>"],"prefix":"10.1002","volume":"55","author":[{"given":"Jaap E.","family":"Borger","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andreas W.","family":"Ehlers","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Lutz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J. Chris","family":"Slootweg","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Koop","family":"Lammertsma","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,11,27]]},"reference":[{"key":"e_1_2_3_1_2","volume-title":"Phosphorus 2000","author":"Corbridge D. E. C.","year":"2000"},{"key":"e_1_2_3_2_2","unstructured":"For reviews see:"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100010e"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2010.12.016"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9003709"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900349u"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b510917e"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403295"},{"key":"e_1_2_3_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403295"},{"key":"e_1_2_3_9_2","unstructured":"The use of bulky main\u2010group radicals has been explored in a number of cases giving similar butterfly\u2010type products. See:"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/B315793H"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0nj00124d"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic301758k"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja207538g"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC02601B"},{"key":"e_1_2_3_15_2","unstructured":"For selected other examples of transition\u2010metal\u2010based radical\u2010type activation of P4giving butterfly species see:"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/om9801148"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC01213E"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404653"},{"key":"e_1_2_3_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201404653"},{"key":"e_1_2_3_19_2","unstructured":"\u00a0"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703055"},{"key":"e_1_2_3_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703055"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902344"},{"key":"e_1_2_3_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902344"},{"key":"e_1_2_3_22_2","unstructured":"\u00a0"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00019F"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804903"},{"key":"e_1_2_3_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804903"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906878q"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302914"},{"key":"e_1_2_3_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201302914"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503065"},{"key":"e_1_2_3_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201503065"},{"key":"e_1_2_3_28_2","unstructured":"Reacting organo\u2010alkali reagents with P4gives complex product mixtures:"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01037a048"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01037a049"},{"key":"e_1_2_3_31_2","doi-asserted-by":"crossref","unstructured":"J. Bresien K. Faust C. Hering\u2010Junghaus J. Rothe A. Schulz A. Villinger Dalton Trans.\u00ad2015 DOI:10.1039\/C5DT02757H.","DOI":"10.1039\/C5DT02757H"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506784"},{"key":"e_1_2_3_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201506784"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405879"},{"key":"e_1_2_3_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201405879"},{"key":"e_1_2_3_34_2","unstructured":"Based on the1H\u2005NMR spectrum recorded immediately after mixing Mes*Li and BPh3in [D8]THF at RT these reagents do not show any direct quenching. However upon standing overnight a reaction does occur showing full conversion to unidentified products."},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/b810189b"},{"key":"e_1_2_3_35_3","unstructured":"\u03c9B97X\u2010D using Gaussian\u200909 (Revision D.01); see the Supporting Information for further details."},{"key":"e_1_2_3_36_2","unstructured":"CCDC\u20051425046 (1\u2009a) 1425047 (3\u2009b) 1425048 (4\u2009b) and 1425049 (5) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge fromThe Cambridge Crystallographic Data Centre."},{"key":"e_1_2_3_37_2","unstructured":"The mixed borane complex [Mes*P4\u22c5(endo\u2010B(C6F5)3)(exo\u2010BPh3)]\u2212could not be detected by31P\u2005NMR spectroscopy."},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic901799q"},{"key":"e_1_2_3_39_2","unstructured":"While theexo exoisomer is the most documented form of bicyclo[1.1.0]tetraphosphabutanes (see Refs.\u2005[3\u20136 \u200914 \u200925]) examples of theexo endoproduct or evidence thereof have been reported:"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198205442"},{"key":"e_1_2_3_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19820940725"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502865"},{"key":"e_1_2_3_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502865"},{"key":"e_1_2_3_42_2","unstructured":"Ref.\u2005[9];"},{"key":"e_1_2_3_43_2","unstructured":"Ref.\u2005[12]."},{"key":"e_1_2_3_44_2","unstructured":"See the Supporting Information for further details."},{"key":"e_1_2_3_45_2","unstructured":"Theendo\u2005isomer could not be detected by31P{1H}\u2005NMR spectroscopy when1was reacted with a \u201cdeficit\u201d (0.8\u2005equiv) of B(C6F5)3in [D8]toluene."},{"key":"e_1_2_3_46_2","unstructured":"The chemical shift differences for the two products detected at \u221260\u2009\u00b0C are in the same range as detected for therac\u2005andmeso\u2005isomers of the symmetrically substituted 1 4\u2010P4[P(N(SiMe3)2(NiPr2)]2 reported by Lappert et\u2005al.[4a] which show three resonance signals for the bridgehead P\u2005atoms (\u03b4=\u2212325.8 (rac) \u2212332.9 (meso) and \u2212338.0\u2005ppm (rac)) and also only one for the wingtip P\u2005atoms (\u2212139.5\u2005ppm)."},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199113531"},{"key":"e_1_2_3_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19911031043"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500892"},{"key":"e_1_2_3_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500892"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201203908"},{"key":"e_1_2_3_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201203908"},{"key":"e_1_2_3_50_2","unstructured":"No monosubstituted product could be detected when only one equivalent of the tungsten precursor was used."},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200300637"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201508916","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201508916","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201508916","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,9]],"date-time":"2023-09-09T15:56:54Z","timestamp":1694275014000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201508916"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,11,27]]},"references-count":66,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2016,1,11]]}},"alternative-id":["10.1002\/anie.201508916"],"URL":"https:\/\/doi.org\/10.1002\/anie.201508916","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,11,27]]}}}