{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T15:16:54Z","timestamp":1790867814828,"version":"4.1.0"},"reference-count":69,"publisher":"Wiley","issue":"28","license":[{"start":{"date-parts":[[2022,5,25]],"date-time":"2022-05-25T00:00:00Z","timestamp":1653436800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/V056069\/1"],"award-info":[{"award-number":["EP\/V056069\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2022,7,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>For several decades, academic researchers have been intensively studying the chemistry of white phosphorus (P<jats:sub>4<\/jats:sub>) in the hope of developing direct methods for its transformation into useful P\u2010containing products. This would bypass the hazardous, multistep procedures currently relied on by industry. However, while academically interesting P<jats:sub>4<\/jats:sub> activation reactions have become well established, their elaboration into useful, general synthetic procedures has remained out of reach. Very recently, however, a series of independent reports has begun to change this state of affairs. Each shows how relatively simple and practical synthetic methods can be used to access academically or industrially relevant P<jats:sub>1<\/jats:sub> compounds from P<jats:sub>4<\/jats:sub> directly, in \u201cone pot\u201d or even in a catalytic fashion. These reports mark a step change in the field of P<jats:sub>4<\/jats:sub> chemistry, and suggest its possible transition from an area of largely academic interest to one with the promise of true synthetic relevance.<\/jats:p>","DOI":"10.1002\/anie.202205019","type":"journal-article","created":{"date-parts":[[2022,4,28]],"date-time":"2022-04-28T11:23:02Z","timestamp":1651144982000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":64,"title":["Recent Breakthroughs in P<sub>4<\/sub> Chemistry: Towards Practical, Direct Transformations into P<sub>1<\/sub> Compounds"],"prefix":"10.1002","volume":"61","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7826-9833","authenticated-orcid":false,"given":"Daniel J.","family":"Scott","sequence":"first","affiliation":[{"name":"Department of Chemistry Chemistry Research Laboratory University of Oxford  12 Mansfield Road Oxford OX1 3TA UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,5,25]]},"reference":[{"key":"e_1_2_5_1_1","volume-title":"Ullmann's Encyclopedia of Industrial Chemistry","author":"Diskowski H.","year":"2020"},{"key":"e_1_2_5_2_1","unstructured":"\u00a0"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11837-007-0071-y"},{"key":"e_1_2_5_4_2","volume-title":"Ullmann's Encyclopedia of Industrial Chemistry","author":"Svara J.","year":"2006"},{"key":"e_1_2_5_5_2","volume-title":"Ullmann's Encyclopedia of Industrial Chemistry","author":"Bettermann G.","year":"2006"},{"key":"e_1_2_5_6_2","volume-title":"Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology","author":"Corbridge D.","year":"1994"},{"key":"e_1_2_5_7_1","unstructured":"Recent academic work has shown that certain P-containing compounds can be made from phosphate derivatives on a laboratory scale without the intermediacy of P4. See:"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.1c01381"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.0c00332"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b01475"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aar6620"},{"key":"e_1_2_5_12_1","unstructured":"For very large scale processes this chloride can be economically re-oxidised to regenerate the Cl2starting material."},{"key":"e_1_2_5_13_1","unstructured":"In principle this disproportionation results in low P atom economy. However in practice these can be valuable products in their own right (e.g. NaH2PO2 produced during alkaline hydrolysis of P4) and in fact are often the target products of such reactions."},{"key":"e_1_2_5_14_1","unstructured":"\u00a0"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC01683A"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470132586.ch48"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19905800126"},{"key":"e_1_2_5_18_1","unstructured":"\u00a0"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9003709"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900349u"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100010e"},{"key":"e_1_2_5_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c07959"},{"key":"e_1_2_5_23_1","unstructured":"\u00a0"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11172-021-3209-0"},{"key":"e_1_2_5_25_2","volume-title":"Phosphorus: The Carbon Copy: From Organophosphorus to Phospha-organic Chemistry","author":"Dillon K. B.","year":"1998"},{"key":"e_1_2_5_26_1","volume-title":"Comprehensive Inorganic Chemistry II: From Elements to Applications","author":"Weigand J. J.","year":"2013"},{"key":"e_1_2_5_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2021.213927"},{"key":"e_1_2_5_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202001854"},{"key":"e_1_2_5_29_1","unstructured":"For an excellent example see"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0461522"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC00615K"},{"key":"e_1_2_5_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202013423"},{"key":"e_1_2_5_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202013423"},{"key":"e_1_2_5_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-020-0518-0"},{"key":"e_1_2_5_34_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2021.2008933"},{"key":"e_1_2_5_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201702067"},{"key":"e_1_2_5_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c01695"},{"key":"e_1_2_5_37_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-019-0378-4"},{"key":"e_1_2_5_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201709766"},{"key":"e_1_2_5_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201709766"},{"key":"e_1_2_5_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b12957"},{"key":"e_1_2_5_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202110619"},{"key":"e_1_2_5_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202110619"},{"key":"e_1_2_5_41_1","unstructured":"\u00a0"},{"key":"e_1_2_5_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00729-7"},{"key":"e_1_2_5_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00058a082"},{"key":"e_1_2_5_44_1","unstructured":"\u00a0"},{"key":"e_1_2_5_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0nj00124d"},{"key":"e_1_2_5_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8QO00943K"},{"key":"e_1_2_5_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8QO01087K"},{"key":"e_1_2_5_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002646"},{"key":"e_1_2_5_49_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC05691C"},{"key":"e_1_2_5_50_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00657-7"},{"key":"e_1_2_5_51_1","unstructured":"For consistency with the proposed mechanism the authors in this study defined turnover with respect to the number of P\u2212P bonds being cleaved. Thus for one equivalent of Bu3SnH to fully transform one equivalent of P4would correspond to six turnovers. Equivalently this means that calculation of the turnover number factors in the 6\u2009:\u20091 ratio of the stoichiometric reaction."},{"key":"e_1_2_5_52_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-26002-7"},{"key":"e_1_2_5_53_1","first-page":"59","volume":"26","author":"Scherer O. J.","year":"1987","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"e_1_2_5_53_2","first-page":"59","volume":"99","year":"1987","journal-title":"Angew. Chem."},{"key":"e_1_2_5_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403581"},{"key":"e_1_2_5_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403581"},{"key":"e_1_2_5_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c11087"},{"key":"e_1_2_5_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197707042"},{"key":"e_1_2_5_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19770891020"},{"key":"e_1_2_5_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19855270803"},{"key":"e_1_2_5_58_1","doi-asserted-by":"publisher","DOI":"10.1515\/pac-2016-1001"},{"key":"e_1_2_5_59_1","unstructured":"Similar transformations of organodilithium reagents into phospholes can be achieved using P4directly. However these reactions form stoichiometric polyphosphide byproducts resulting in very poor P atom economy.[14]"},{"key":"e_1_2_5_60_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-022-00913-4"},{"key":"e_1_2_5_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405196"},{"key":"e_1_2_5_62_1","first-page":"362","volume":"14","author":"Gr\u00fctzmacher H.","year":"2022","journal-title":"Nat. Chem."},{"key":"e_1_2_5_63_1","unstructured":"Wolf's PRC system is most sensibly interpreted as using radicals to functionalize the \u201cP0\u201d synthon P4. Strictly speaking it could also be considered to use P4as a source of \u201cP3\u2212\u201d as similarly to Wolf and Scott's hydrostannylation method it too involves net reduction and electrophilic substrates (aryl iodides). 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