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Here, we investigated the de\/re\u2010aromatisation of pyridine facilitated by pyridylamino\u2010functionalised silylene reactions with ketones and ketene. The reactivity outcome is highly dependent on the substituents on the ketones. By carefully tuning the steric demand of the ketone, each intermediate of the reaction sequence could be isolated. At room temperature, benzophenone and acetophenone substrates led to dearomatisation of the pyridine moiety, with the case of acetophenone showing an intermediate silaoxirane preceding dearomatisation. However, when subjected to acetone or diphenylketene, only silaoxiranes were formed without dearomatisation of the pyridine moiety. Notably, only benzophenone\u2010derived dearomatised species demonstrated rearomatisation upon heating. Furthermore, the reduced steric bulk of the ketene facilitated further ring expansion with another equivalent of the substrate, forming sila\u20101,3\u2010dioxolanes. Both steric hindrance and aromatic groups collectively influence the dearomatisation of pyridine in pyridylaminosilylene reactions.<\/jats:p>","DOI":"10.1002\/chem.202402456","type":"journal-article","created":{"date-parts":[[2024,7,2]],"date-time":"2024-07-02T10:09:59Z","timestamp":1719914999000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["De\u2010 and Rearomatisation of Pyridine in Silylene Chemistry"],"prefix":"10.1002","volume":"30","author":[{"given":"Da","family":"Jin","sequence":"first","affiliation":[{"name":"Institute of Inorganic Chemistry (AOC) Karlsruhe Institute of Technology (KIT)  Kaiserstr. 12 76131 Karlsruhe Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7831-1410","authenticated-orcid":false,"given":"Alexander","family":"Hinz","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry (AOC) Karlsruhe Institute of 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