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The incorporation of phosphorus atom into \u03c0\u2010conjugated frameworks offers unique opportunities for controlling the properties of derived species. A phosphorus analogue of <jats:italic>p<\/jats:italic>\u2010quinodimethane (<jats:italic>p<\/jats:italic>QDM), (IPrC)<jats:sub>2<\/jats:sub>P<jats:sub>4<\/jats:sub> [<jats:bold>5<\/jats:bold>, IPr=C{N(Ar)CH<jats:sub>2<\/jats:sub>}<jats:sub>2<\/jats:sub>; Ar=2,6\u2010<jats:italic>i<\/jats:italic>Pr<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>3<\/jats:sub>] featuring a planar P<jats:sub>4<\/jats:sub> ring, was readily accessible by KC<jats:sub>8<\/jats:sub>\u2010reduction of (IPrC)(PCl<jats:sub>2<\/jats:sub>)<jats:sub>2<\/jats:sub> (<jats:bold>2<\/jats:bold>). Base\u2010mediated C\u2212H functionalization of IPrCH<jats:sub>2<\/jats:sub> (<jats:bold>1<\/jats:bold>) with PCl<jats:sub>3<\/jats:sub> afforded <jats:bold>2<\/jats:bold>. The formation of <jats:bold>5<\/jats:bold> was expected to occur through a dimerization of the transient 3H\u2010diphosphirene (IPrC)P<jats:sub>2<\/jats:sub> (<jats:bold>4<\/jats:bold>), which was theoretically suggested to have an intermediate diradical character. Compound <jats:bold>5<\/jats:bold> underwent photo\u2010induced ring\u2010contraction reaction to form the singlet diradicaloid (IPrCP)<jats:sub>2<\/jats:sub> <jats:bold>VI<\/jats:bold> and white phosphorus (P<jats:sub>4<\/jats:sub>). The formation of and <jats:bold>VI<\/jats:bold> and P<jats:sub>4<\/jats:sub> suggested the formal diphosphorus (P<jats:sub>2<\/jats:sub>) elimination from <jats:bold>5<\/jats:bold>. Indeed, photolysis of a mixture of 1,3\u2010cyclohexadiene (CHD) and <jats:bold>5<\/jats:bold> led to the formation of P<jats:sub>2<\/jats:sub>\u2010entrapped product (CHD)<jats:sub>2<\/jats:sub>P<jats:sub>2<\/jats:sub> (<jats:bold>6<\/jats:bold>). The compound <jats:bold>5<\/jats:bold> represents the first organophosphorus species that functions as a P<jats:sub>2<\/jats:sub> source.<\/jats:p>","DOI":"10.1002\/chem.201805932","type":"journal-article","created":{"date-parts":[[2019,2,5]],"date-time":"2019-02-05T04:30:44Z","timestamp":1549341044000},"page":"3244-3247","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["A Phosphorus Analogue of <i>p<\/i>\u2010Quinodimethane with a Planar P<sub>4<\/sub> Ring: A Metal\u2010Free Diphosphorus Source"],"prefix":"10.1002","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4810-9203","authenticated-orcid":false,"given":"Dennis","family":"Rottsch\u00e4fer","sequence":"first","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beate","family":"Neumann","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hans\u2010Georg","family":"Stammler","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6005-7629","authenticated-orcid":false,"given":"Ryohei","family":"Kishi","sequence":"additional","affiliation":[{"name":"Department of Materials Engineering Science, Graduate School of, Engineering Science Osaka University  Toyonaka Osaka 560-8531 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3544-1290","authenticated-orcid":false,"given":"Masayoshi","family":"Nakano","sequence":"additional","affiliation":[{"name":"Department of Materials Engineering Science, Graduate School of, Engineering Science Osaka University  Toyonaka Osaka 560-8531 Japan"},{"name":"Institute for Molecular Science  38 Nishigo-Naka, Myodaiji Okazaki 444-8585 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2146-5432","authenticated-orcid":false,"given":"Rajendra S.","family":"Ghadwal","sequence":"additional","affiliation":[{"name":"Anorganische Molek\u00fclchemie und Katalyse, Anorganische Chemie und Strukturchemie, Centrum f\u00fcr Molekulare Materialien, Fakult\u00e4t f\u00fcr Chemie Universit\u00e4t Bielefeld  Universit\u00e4tsstrasse 25 33615 Bielefeld Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,2,4]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900100"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200900100"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1351\/PAC-CON-12-09-13"},{"key":"e_1_2_2_4_2","volume-title":"Phosphorus: The Carbon Copy","author":"Dillon K. 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