{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T01:20:51Z","timestamp":1760404851156,"version":"build-2065373602"},"reference-count":55,"publisher":"Wiley","issue":"25","license":[{"start":{"date-parts":[[2021,4,12]],"date-time":"2021-04-12T00:00:00Z","timestamp":1618185600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,5,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A 1,2\u2010dicarbonyl moiety on a cage\u2010opened fullerene skeleton is one of suitable building blocks for the further derivatization. Herein, we discuss the chemical transformation of a 1,2\u2010dicarbonyl compound into <jats:italic>\u03b2<\/jats:italic>\u2010oxo\u2010phosphorus ylide, acid anhydride, and <jats:italic>\u03b1<\/jats:italic>\u2010methylene carbonyl derivatives. Despite possessing a sterically small methylene unit in the last one, the release of an encapsulated water molecule was significantly supressed whereas the <jats:italic>\u03b2<\/jats:italic>\u2010oxo\u2010phosphorus ylide bearing three bulky <jats:italic>p<\/jats:italic>\u2010tolyl groups on the P\u2010atom enabled the faster insertion\/release dynamics, implying the flexibility of the phosphonium substituent. The replacement of the carbonyl group with phosphorus ylide and methylene units largely varied electrochemical properties of the fullerene skeleton, likely arising from the anionic charge delocalized over the entire molecule and removal of an electron\u2010withdrawable carbonyl group, respectively.<\/jats:p>","DOI":"10.1002\/chem.202100640","type":"journal-article","created":{"date-parts":[[2021,4,9]],"date-time":"2021-04-09T12:55:30Z","timestamp":1617972930000},"page":"7235-7238","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Reactions on a 1,2\u2010Dicarbonyl Moiety of a Fullerene Skeleton"],"prefix":"10.1002","volume":"27","author":[{"given":"Yoshifumi","family":"Hashikawa","sequence":"first","affiliation":[{"name":"Institute for Chemical Research Kyoto University  611-0011 Uji Kyoto Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jiayue","family":"Li","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  611-0011 Uji Kyoto Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shu","family":"Okamoto","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  611-0011 Uji Kyoto Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0287-0299","authenticated-orcid":false,"given":"Yasujiro","family":"Murata","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  611-0011 Uji Kyoto Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,4,12]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0000325"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc30691c"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules18032942"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10593-015-1717-2"},{"key":"e_1_2_2_6_1","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","first-page":"466","volume":"121","author":"Kukhtin V. A.","year":"1958","journal-title":"Dokl. Akad. Nauk."},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01495a073"},{"key":"e_1_2_2_9_1","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.10.023"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000023"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01495a073"},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19535800107"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.210.4470.600"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b811738a"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/B913766A"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/poc.3169"},{"key":"e_1_2_2_20_1","unstructured":"\u00a0"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo026033"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0763798"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc02750b"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c10676"},{"key":"e_1_2_2_25_1","unstructured":"\u00a0"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004879"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004879"},{"key":"e_1_2_2_26_4","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004879"},{"key":"e_1_2_2_26_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004879"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9QO00188C"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201100745"},{"journal-title":"Chem. Eur. J.","year":"2021","author":"Hashikawa Y.","key":"e_1_2_2_29_1"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC06198E"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1139\/cjc-2016-0465"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-020-00340-x"},{"key":"e_1_2_2_34_1","unstructured":"\u00a0"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1206376"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol501113y"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2563"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b09459"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QM00449D"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201900983"},{"key":"e_1_2_2_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201900983"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.190874"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA09067K"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527613908"},{"key":"e_1_2_2_44_1","unstructured":"\u00a0"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010166f"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701212"},{"key":"e_1_2_2_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201701212"},{"key":"e_1_2_2_46_4","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201701212"},{"key":"e_1_2_2_46_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701212"},{"key":"e_1_2_2_47_1","unstructured":"Deposition Number(s) 2063078 (for H2O@2)contain(s) the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures servicewww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_2_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cp20404a"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100640","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202100640","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100640","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T11:03:53Z","timestamp":1760267033000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202100640"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,4,12]]},"references-count":55,"journal-issue":{"issue":"25","published-print":{"date-parts":[[2021,5,3]]}},"alternative-id":["10.1002\/chem.202100640"],"URL":"https:\/\/doi.org\/10.1002\/chem.202100640","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2021,4,12]]},"assertion":[{"value":"2021-02-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-04-12","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}