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However, a lack of isolated examples due to their lability has hampered in-depth understanding of structures and their reaction mechanisms. In this study, we crystallographically reveal the solid-state structure of a phosha-Michael adduct engaged in a cage-opened C<jats:sub>60<\/jats:sub> skeleton, which is formed as a kinetic product. This compound exhibits dark brown colour in solution with an intense absorption band that extends to 1000\u2009nm, reflecting intramolecular charge transfer transitions. From the 1,2-dicarbonyl moiety on the conjugated orifice, \u03b2-oxo-phosphorus ylide is formed as a thermodynamic product. The reaction mechanism that has long been disputed is examined by experimental and theoretical studies, showing a pathway which includes an S<jats:sub>N<\/jats:sub>2 reaction as a key step instead of the\u00a0hitherto considered carbene pathway.<\/jats:p>","DOI":"10.1038\/s42004-020-00340-x","type":"journal-article","created":{"date-parts":[[2020,7,21]],"date-time":"2020-07-21T10:02:52Z","timestamp":1595325772000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["Organophosphorus zwitterions engaged in a conjugated macrocycle on fullerene"],"prefix":"10.1038","volume":"3","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7834-9593","authenticated-orcid":false,"given":"Yoshifumi","family":"Hashikawa","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shu","family":"Okamoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0287-0299","authenticated-orcid":false,"given":"Yasujiro","family":"Murata","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2020,7,21]]},"reference":[{"key":"340_CR1","doi-asserted-by":"publisher","first-page":"44","DOI":"10.1002\/jlac.19535800107","volume":"580","author":"G Wittig","year":"1953","unstructured":"Wittig, G. & Geisslerg, G. 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