{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T00:57:35Z","timestamp":1788397055080,"version":"build-2803163510"},"reference-count":90,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2019,2,18]],"date-time":"2019-02-18T00:00:00Z","timestamp":1550448000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2019,3,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The reaction of Na[OCP] with (R<jats:sub>2<\/jats:sub>N)<jats:sub>2<\/jats:sub>ECl (E=P or As; R=alkyl) granted direct access to transient amine\u2010substituted diphospha\u2010 and arsaphospha\u2010acrylamide analogues, (R<jats:sub>2<\/jats:sub>N)E=P(CONR<jats:sub>2<\/jats:sub>) <jats:bold>1<\/jats:bold>. Their facile formation allowed for a comprehensive reactivity study. Dimerization yielded the four\u2010membered rings (R<jats:sub>2<\/jats:sub>N)<jats:sub>2<\/jats:sub>E<jats:sub>2<\/jats:sub>P<jats:sub>2<\/jats:sub>(CONR<jats:sub>2<\/jats:sub>)<jats:sub>2<\/jats:sub>, whereas in the presence of excess Na[OCP], a stepwise [2+2] cycloaddition occured, leading to the sodium salts of carboxotripnictides [(R<jats:sub>2<\/jats:sub>N)EP<jats:sub>2<\/jats:sub>CO(CONR<jats:sub>2<\/jats:sub>)]<jats:sup>\u2212<\/jats:sup>. These salts served as a reservoir of <jats:bold>1<\/jats:bold>, either by extrusion of Na[OCP] or by reaction with the appropriate (R<jats:sub>2<\/jats:sub>N)<jats:sub>2<\/jats:sub>ECl, giving the [4+2]\u2010cycloaddition products (R<jats:sub>2<\/jats:sub>N)EP(C<jats:sub>6<\/jats:sub>H<jats:sub>10<\/jats:sub>)(CONR<jats:sub>2<\/jats:sub>) in the presence of 2,3\u2010dimethylbutadiene. The formal conjugate addition product K[(<jats:italic>t<\/jats:italic>BuO)(R<jats:sub>2<\/jats:sub>N)PP(CONR<jats:sub>2<\/jats:sub>)] was obtained by reaction of Na[(R<jats:sub>2<\/jats:sub>N)PP<jats:sub>2<\/jats:sub>CO(CONR<jats:sub>2<\/jats:sub>)] with <jats:italic>t<\/jats:italic>BuOK. In addition, a rare diphosphadigalletane with a ladder\u2010type (R<jats:sub>2<\/jats:sub>N)<jats:sub>2<\/jats:sub>Ga<jats:sub>2<\/jats:sub>P<jats:sub>2<\/jats:sub>(CONR<jats:sub>2<\/jats:sub>)<jats:sub>2<\/jats:sub> core was isolated from the reaction of Na[OCP] with (R<jats:sub>2<\/jats:sub>N)<jats:sub>2<\/jats:sub>GaCl (R=alkyl). The unprecedented pnictogenyl carboxamide compounds were thoroughly characterized, including single\u2010crystal X\u2010ray structure determinations, and mechanisms for their formation were investigated by DFT calculations.<\/jats:p>","DOI":"10.1002\/chem.201806116","type":"journal-article","created":{"date-parts":[[2019,1,15]],"date-time":"2019-01-15T11:53:01Z","timestamp":1547553181000},"page":"3957-3962","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Transient Dipnictyl Analogues of Acrylamides, R\u2212E=E\u2032\u2212CONR<sub>2<\/sub>, and a Related Diphosphadigalletane from Na[OCP] and (R<sub>2<\/sub>N)<sub>2<\/sub>ECl (E, E\u2032=P, As, Ga)"],"prefix":"10.1002","volume":"25","author":[{"given":"Jaap E.","family":"Borger","sequence":"first","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog Weg 1 H\u00f6nggerberg 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gr\u00e9goire","family":"Le\u2005Corre","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog Weg 1 H\u00f6nggerberg 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanbo","family":"Mei","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog Weg 1 H\u00f6nggerberg 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Riccardo","family":"Suter","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog Weg 1 H\u00f6nggerberg 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Erik","family":"Schrader","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog Weg 1 H\u00f6nggerberg 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1531-8906","authenticated-orcid":false,"given":"Hansj\u00f6rg","family":"Gr\u00fctzmacher","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog Weg 1 H\u00f6nggerberg 8093 Z\u00fcrich Switzerland"},{"name":"School of Chemistry Lehn Institute of Functional Materials (LIFM) Sun Yat-sen University  135 West Xingang Road Guangzhou 510275 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,2,18]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"crossref","DOI":"10.1093\/hesc\/9780199270293.001.0001","volume-title":"Organic Chemistry","author":"Clayden J.","year":"2012"},{"key":"e_1_2_6_2_1","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","volume-title":"Multiple Bonds and Low Coordination in Phosphorus Chemistry","author":"Regitz M.","year":"1990"},{"key":"e_1_2_6_4_2","volume-title":"Phosphorus: The Carbon Copy","author":"Dillon K. B.","year":"1998"},{"key":"e_1_2_6_5_1","volume-title":"Phosphorus 2000","author":"Corbridge D. E. C.","year":"2000"},{"key":"e_1_2_6_6_1","unstructured":"For reviews concerning diphosphene chemistry see:"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00016a008"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9408989"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201500990"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103634"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103634"},{"key":"e_1_2_6_10_3","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC07654A"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19926120113"},{"key":"e_1_2_6_12_1","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201102930"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201102930"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3DT52359D"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2011.07.016"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201305235"},{"key":"e_1_2_6_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201305235"},{"key":"e_1_2_6_17_1","unstructured":"For reviews see:"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201803888"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201800179"},{"key":"e_1_2_6_20_1","unstructured":"For selected examples 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examples where the phosphaketene is coordinated to a transition metal see:"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201202590"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC02150B"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201501075"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC04504E"},{"key":"e_1_2_6_39_1","unstructured":"For examples where the phosphaketene is substituted by group-14 compounds see:"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3dt53569j"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600701"},{"key":"e_1_2_6_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201600701"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201511956"},{"key":"e_1_2_6_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201511956"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.6b00187"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701337"},{"key":"e_1_2_6_44_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201701337"},{"key":"e_1_2_6_45_1","unstructured":"Although thermally stable Iyields elusive phosphinidenes by extrusion of CO upon UV irradiation see:"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2016.04.001"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04232"},{"key":"e_1_2_6_47_3","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11496"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4DT04012K"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201600903"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201600903"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800987"},{"key":"e_1_2_6_51_1","unstructured":"\u00a0"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1515\/znb-1991-0705"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja502675d"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0365110X62001450"},{"key":"e_1_2_6_55_2","unstructured":"Ref.\u2005[19];"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403631"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301137"},{"key":"e_1_2_6_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301137"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1524\/zkri.1996.211.5.343"},{"key":"e_1_2_6_59_1","unstructured":"CCDC\u20051579440\u2005(2) 1579438\u2005(Na[3]) 1579437\u2005(Na[4]) 1579439\u2005(5) 1815678\u2005(7) 1815677\u2005(Na[8]) 1815676\u2005(9) and 1860719\u2005(10) contain the supplementary crystallographic data for this paper. These data are provided free of charge byThe Cambridge Crystallographic Data Centre."},{"key":"e_1_2_6_60_1","unstructured":"For example see:"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703055"},{"key":"e_1_2_6_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703055"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004385"},{"key":"e_1_2_6_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004385"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b02462"},{"key":"e_1_2_6_64_1","unstructured":"Na[3] also forms as a side product in the reaction towards2."},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200901472"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC04610B"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3dt50599e"},{"key":"e_1_2_6_68_1","unstructured":"See the Supporting Information for further details."},{"key":"e_1_2_6_69_1","unstructured":"For known examples see:"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00018a061"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0303284"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.inoche.2005.06.006"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5DT03889H"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201806116","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201806116","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.201806116","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201806116","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T14:30:25Z","timestamp":1760279425000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201806116"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,2,18]]},"references-count":90,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2019,3,12]]}},"alternative-id":["10.1002\/chem.201806116"],"URL":"https:\/\/doi.org\/10.1002\/chem.201806116","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,2,18]]},"assertion":[{"value":"2018-12-10","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-02-18","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}