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Characterization of the former by structural and computational methods reveals an unprecedented extent of alkyne activation by a formal chromium(II) center, suggesting that this complex is best described as a chromium(IV)\u2010metallocyclopropene. Exposure of this compound to 4,4\u2032\u2010difluoroazobenzene results in the formation of a chromium(VI) diimido complex, which constitutes a rare 4\u2010electron oxidative addition of an N=N double bond. The isolation of a chromium(IV)\u2010hydrazido intermediate enabled mechanistic investigations of this challenging bond cleavage process. This work substantiates the notion that terminal phosphinimide ligands can engender first\u2010row transition metal ions with exceptional reactivity.<\/jats:p>","DOI":"10.1002\/anie.202310482","type":"journal-article","created":{"date-parts":[[2023,9,1]],"date-time":"2023-09-01T14:58:50Z","timestamp":1693580330000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Four\u2010Electron Oxidative Addition of an N=N Double Bond at a Chromium Metallocyclopropene**"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7517-0448","authenticated-orcid":false,"given":"Paul","family":"Rathke","sequence":"first","affiliation":[{"name":"College of Chemistry University of California Berkeley  Berkeley CA 94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6241-6253","authenticated-orcid":false,"given":"Jonathan","family":"Rittle","sequence":"additional","affiliation":[{"name":"College of Chemistry University of California Berkeley  Berkeley CA 94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,9,18]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"J.\u2005F. 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