{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:57:28Z","timestamp":1760317048575,"version":"build-2065373602"},"reference-count":61,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2017,12,7]],"date-time":"2017-12-07T00:00:00Z","timestamp":1512604800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","award":["RGPIN-2016-04457"],"award-info":[{"award-number":["RGPIN-2016-04457"]}],"id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2018,1,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The phosphorus\u2013sulfur heterocycles 1,2\u2010thiaphosphetenes and phosphirene sulfides have been prepared, and represent the first structurally characterized derivatives for either class of compound. These strained P\u2212S ring systems are formed by the reaction of a phosphinidene sulfide and alkyne. Using an internal alkyne, only the 3\u2010membered P<jats:sup>V<\/jats:sup>, phosphirene sulfide was produced, whereas a terminal alkyne yielded a mixture of phosphirene sulfide and 1,2\u2010thiaphosphetene (P<jats:sup>III<\/jats:sup>). Detailed computational analysis revealed that for numerous derivatives of alkynes, the corresponding 4\u2010membered rings are always more stable than the 3\u2010membered isomers. The electronic nature of \u201cfree\u201d phosphinidene sulfides (R\u2212P=S) is discussed based on computational results.<\/jats:p>","DOI":"10.1002\/chem.201705198","type":"journal-article","created":{"date-parts":[[2017,11,6]],"date-time":"2017-11-06T09:16:40Z","timestamp":1509959800000},"page":"743-749","source":"Crossref","is-referenced-by-count":12,"title":["Addressing the Nature of Phosphinidene Sulfides via the Synthesis of P\u2212S Heterocycles"],"prefix":"10.1002","volume":"24","author":[{"given":"Cameron M. E.","family":"Graham","sequence":"first","affiliation":[{"name":"Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research Western University  1151\u2005Richmond St. London Ontario N6A 5B7 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Charles L. B.","family":"Macdonald","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of Windsor  401\u2005Sunset Ave. Windsor ON N9B 3P4 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paul D.","family":"Boyle","sequence":"additional","affiliation":[{"name":"Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research Western University  1151\u2005Richmond St. London Ontario N6A 5B7 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"James A.","family":"Wisner","sequence":"additional","affiliation":[{"name":"Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research Western University  1151\u2005Richmond St. London Ontario N6A 5B7 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2727-7635","authenticated-orcid":false,"given":"Paul J.","family":"Ragogna","sequence":"additional","affiliation":[{"name":"Department of Chemistry and the Centre for Advanced Materials and Biomaterials Research Western University  1151\u2005Richmond St. London Ontario N6A 5B7 Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2017,12,7]]},"reference":[{"doi-asserted-by":"publisher","key":"e_1_2_2_1_1","DOI":"10.1021\/ja00749a044"},{"doi-asserted-by":"publisher","key":"e_1_2_2_2_1","DOI":"10.1021\/ja00798a066"},{"doi-asserted-by":"publisher","key":"e_1_2_2_3_1","DOI":"10.1002\/jlac.19535800107"},{"doi-asserted-by":"publisher","key":"e_1_2_2_4_1","DOI":"10.1002\/cber.19540870919"},{"doi-asserted-by":"publisher","key":"e_1_2_2_5_1","DOI":"10.1021\/cr00094a007"},{"doi-asserted-by":"publisher","key":"e_1_2_2_6_1","DOI":"10.1002\/9783527613908"},{"doi-asserted-by":"publisher","key":"e_1_2_2_7_1","DOI":"10.1039\/c3cs60105f"},{"doi-asserted-by":"publisher","key":"e_1_2_2_8_1","DOI":"10.1080\/10426507.2014.974100"},{"doi-asserted-by":"publisher","key":"e_1_2_2_9_1","DOI":"10.1021\/ja056650q"},{"doi-asserted-by":"publisher","key":"e_1_2_2_10_1","DOI":"10.1002\/anie.201404877"},{"doi-asserted-by":"publisher","key":"e_1_2_2_10_2","DOI":"10.1002\/ange.201404877"},{"doi-asserted-by":"publisher","key":"e_1_2_2_11_1","DOI":"10.1039\/C6CC04667C"},{"doi-asserted-by":"publisher","key":"e_1_2_2_12_1","DOI":"10.1021\/acs.organomet.5b00974"},{"doi-asserted-by":"publisher","key":"e_1_2_2_13_1","DOI":"10.1039\/C7DT00136C"},{"doi-asserted-by":"publisher","key":"e_1_2_2_14_1","DOI":"10.1021\/ja00036a078"},{"doi-asserted-by":"publisher","key":"e_1_2_2_15_1","DOI":"10.1002\/anie.199725001"},{"key":"e_1_2_2_15_2","doi-asserted-by":"crossref","first-page":"2609","DOI":"10.1002\/ange.19971092230","volume":"109","year":"1997","journal-title":"Angew. Chem."},{"doi-asserted-by":"publisher","key":"e_1_2_2_16_1","DOI":"10.1021\/ja00089a063"},{"doi-asserted-by":"publisher","key":"e_1_2_2_17_1","DOI":"10.1002\/anie.199308691"},{"doi-asserted-by":"publisher","key":"e_1_2_2_17_2","DOI":"10.1002\/ange.19931050634"},{"doi-asserted-by":"publisher","key":"e_1_2_2_18_1","DOI":"10.1039\/a808918c"},{"doi-asserted-by":"publisher","key":"e_1_2_2_19_1","DOI":"10.1039\/a607889c"},{"doi-asserted-by":"publisher","key":"e_1_2_2_20_1","DOI":"10.1021\/ja9720669"},{"doi-asserted-by":"publisher","key":"e_1_2_2_21_1","DOI":"10.1021\/ja00132a049"},{"doi-asserted-by":"publisher","key":"e_1_2_2_22_1","DOI":"10.1080\/10426509908546204"},{"doi-asserted-by":"publisher","key":"e_1_2_2_23_1","DOI":"10.1039\/C29710001186"},{"doi-asserted-by":"publisher","key":"e_1_2_2_24_1","DOI":"10.1016\/S0040-4020(99)00779-6"},{"doi-asserted-by":"publisher","key":"e_1_2_2_25_1","DOI":"10.1039\/P19730002065"},{"doi-asserted-by":"publisher","key":"e_1_2_2_26_1","DOI":"10.1515\/znb-1986-0719"},{"doi-asserted-by":"publisher","key":"e_1_2_2_27_1","DOI":"10.1021\/ja00538a018"},{"doi-asserted-by":"publisher","key":"e_1_2_2_28_1","DOI":"10.1039\/p19730002069"},{"doi-asserted-by":"publisher","key":"e_1_2_2_29_1","DOI":"10.1246\/bcsj.48.546"},{"doi-asserted-by":"publisher","key":"e_1_2_2_30_1","DOI":"10.1021\/om500828n"},{"doi-asserted-by":"publisher","key":"e_1_2_2_31_1","DOI":"10.1002\/anie.201611196"},{"doi-asserted-by":"publisher","key":"e_1_2_2_31_2","DOI":"10.1002\/ange.201611196"},{"unstructured":"See the Supporting Information for synthetic detail and characterization for [2+4] cycloaddition with Ch=S.","key":"e_1_2_2_32_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_33_1","DOI":"10.1039\/c39840000045"},{"doi-asserted-by":"publisher","key":"e_1_2_2_34_1","DOI":"10.1039\/C39950002507"},{"doi-asserted-by":"publisher","key":"e_1_2_2_35_1","DOI":"10.1039\/a904150h"},{"doi-asserted-by":"publisher","key":"e_1_2_2_36_1","DOI":"10.1021\/om401050w"},{"doi-asserted-by":"publisher","key":"e_1_2_2_37_1","DOI":"10.1002\/anie.201504869"},{"doi-asserted-by":"publisher","key":"e_1_2_2_37_2","DOI":"10.1002\/ange.201504869"},{"doi-asserted-by":"publisher","key":"e_1_2_2_38_1","DOI":"10.1021\/acs.organomet.6b00227"},{"doi-asserted-by":"publisher","key":"e_1_2_2_39_1","DOI":"10.1021\/jacs.7b05464"},{"doi-asserted-by":"publisher","key":"e_1_2_2_40_1","DOI":"10.1080\/10426509908546235"},{"doi-asserted-by":"publisher","key":"e_1_2_2_41_1","DOI":"10.1021\/ja00302a016"},{"unstructured":"Reaction proceeds at room temperature and full conversion was reached after 36\u2005h. Gentle heating at 80\u2009\u00b0C leads to full conversion after 16\u2005h.","key":"e_1_2_2_42_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_43_1","DOI":"10.1039\/C39820000569"},{"doi-asserted-by":"publisher","key":"e_1_2_2_44_1","DOI":"10.1016\/S0040-4039(00)81487-2"},{"doi-asserted-by":"publisher","key":"e_1_2_2_45_1","DOI":"10.1021\/jo00346a041"},{"unstructured":"SMART Bruker AXS INC Madison WI 2001.","key":"e_1_2_2_46_1"},{"unstructured":"COLLECT Nonius BV Delft The Netherlands 2001.","key":"e_1_2_2_47_1"},{"unstructured":"SAINT v2013.8 Bruker AXS INC Madison WI USA 2013.","key":"e_1_2_2_48_1"},{"unstructured":"SADABS v2012.1 Bruker AXS INC Madison WI USA 2012.","key":"e_1_2_2_49_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_50_1","DOI":"10.1107\/S2053273314026370"},{"doi-asserted-by":"publisher","key":"e_1_2_2_51_1","DOI":"10.1107\/S2053229614026540"},{"doi-asserted-by":"crossref","unstructured":"A. Spek ACTA Crystallogr.2009 D65 148.","key":"e_1_2_2_52_1","DOI":"10.1107\/S090744490804362X"},{"unstructured":"Gaussian\u200509 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Caricato X. Li H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005J.\u2005A. Montgomery J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi N. Rega N.\u2005J. Millam M. Klene J.\u2005E. Knox J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels \u00d6. Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski D.\u2005J. Fox Gaussian Inc.: Wallingford CT 2009.","key":"e_1_2_2_53_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_54_1","DOI":"10.1007\/s00214-007-0310-x"},{"doi-asserted-by":"publisher","key":"e_1_2_2_55_1","DOI":"10.1063\/1.467146"},{"volume-title":"Theoretical Chemistry Institute, University of Wisconsin","year":"2013","author":"Glendening E.","key":"e_1_2_2_56_1"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201705198","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201705198","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:23:50Z","timestamp":1760300630000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201705198"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,12,7]]},"references-count":61,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2018,1,12]]}},"alternative-id":["10.1002\/chem.201705198"],"URL":"https:\/\/doi.org\/10.1002\/chem.201705198","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2017,12,7]]}}}