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Photolysis of compound <jats:bold>2<\/jats:bold> results in the formation of CAAC\u2010stabilized BP\u2010doped phenanthryne (<jats:bold>3<\/jats:bold>) through tandem decarbonylation, monoatomic phosphide insertion, and ring\u2010expansion. Notably, while BN\u2010doped phenanthryne was previously discussed as a reactive intermediate which could not be isolated, the heavier BP\u2010doped analogue exhibits remarkable solution and solid\u2010state stability. The reactivity of <jats:bold>2<\/jats:bold> with stable carbenes was also explored. Addition of CAAC to <jats:bold>2<\/jats:bold> led to migration of the original CAAC ligand from boron to phosphorus and coordination of the added CAAC to carbon, affording compound <jats:bold>4<\/jats:bold>. Reaction of 1,3\u2010diisopropyl\u20104,5\u2010dimethylimidazol\u20102\u2010ylidene (NHC) with <jats:bold>2<\/jats:bold> resulted in N\u2212C bond activation to give the unusual spiro\u2010heterocyclic compound (<jats:bold>5<\/jats:bold>).<\/jats:p>","DOI":"10.1002\/anie.201916362","type":"journal-article","created":{"date-parts":[[2020,1,8]],"date-time":"2020-01-08T03:50:08Z","timestamp":1578455408000},"page":"3971-3975","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":69,"title":["Crystalline BP\u2010Doped Phenanthryne via Photolysis of The Elusive Boraphosphaketene"],"prefix":"10.1002","volume":"59","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9017-7728","authenticated-orcid":false,"given":"Wenlong","family":"Yang","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Virginia  409 McCormick Rd.\/ PO Box 400319 Charlottesville VA 22904 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0464-8010","authenticated-orcid":false,"given":"Kelsie E.","family":"Krantz","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Virginia  409 McCormick Rd.\/ PO Box 400319 Charlottesville VA 22904 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0939-3309","authenticated-orcid":false,"given":"Diane A.","family":"Dickie","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Virginia  409 McCormick Rd.\/ PO Box 400319 Charlottesville VA 22904 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0954-9054","authenticated-orcid":false,"given":"Andrew","family":"Molino","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Physics La Trobe Institute for Molecular Science La Trobe University  Melbourne 3086 Victoria Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0007-4486","authenticated-orcid":false,"given":"David J. 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