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Using two model systems, non\u2010Kekul\u00e9 triangulene\u20104,8\u2010dione and Kekul\u00e9 anthanthrone, we identify unexpected regioselectivities and uncover the rules that govern these reactions. Considering the large number of nanographene ketones that have been reported since the pioneering work of Eric Clar, this method enables synthesis and exploration of hitherto unknown functionalized nanographenes.<\/jats:p>","DOI":"10.1002\/anie.202016437","type":"journal-article","created":{"date-parts":[[2021,3,1]],"date-time":"2021-03-01T07:50:36Z","timestamp":1614585036000},"page":"13521-13528","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Rules of Nucleophilic Additions to Zigzag Nanographene Diones**"],"prefix":"10.1002","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7854-1307","authenticated-orcid":false,"given":"Peter","family":"Ribar","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Basel  St. Johanns-Ring 19 4056 Basel Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0934-3627","authenticated-orcid":false,"given":"Leo\u0161","family":"Valenta","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Zurich  Winterthurerstrasse 190 8057 Zurich Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0013-4116","authenticated-orcid":false,"given":"Tom\u00e1\u0161","family":"\u0160olomek","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Basel  St. Johanns-Ring 19 4056 Basel Switzerland"},{"name":"Prievidza Chemical Society  M. Hod\u017eu 10\/16 971 01 Prievidza Slovak Republic"},{"name":"Current address: Department of Chemistry, Biochemistry and Pharmaceutical Sciences University of Bern  Freiestrasse 3 3012 Bern Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5595-431X","authenticated-orcid":false,"given":"Michal","family":"Jur\u00ed\u010dek","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Zurich  Winterthurerstrasse 190 8057 Zurich Switzerland"},{"name":"Prievidza Chemical Society  M. 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The term \u201czigzag nanographene\u201d refers to systems in which all edges are zigzag. For example triangulene and anthanthrene have three and four zigzag edges respectively."},{"key":"e_1_2_6_42_1","unstructured":"\u00a0"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC01986C"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b09075"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201802818"},{"key":"e_1_2_6_45_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201802818"},{"key":"e_1_2_6_46_1","unstructured":"\u00a0"},{"key":"e_1_2_6_47_2","volume-title":"Polycyclic Hydrocarbons, Vol.\u20051","author":"Clar E.","year":"1964"},{"key":"e_1_2_6_48_2","volume-title":"Polycyclic Hydrocarbons, Vol.\u20052","author":"Clar E.","year":"1964"},{"key":"e_1_2_6_49_1","unstructured":"Examples with lithium acetylide:"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801886h"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol701642j"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/b502950c"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b09337"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2000099"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900838a"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja804515y"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.polymer.2017.07.034"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.orgel.2014.11.025"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol100178s"},{"key":"e_1_2_6_60_1","unstructured":"\u00a0"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo402674m"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3sc50645b"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201202878"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2JM14998B"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp052337z"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1038\/nnano.2016.305"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01107a035"},{"key":"e_1_2_6_68_1","unstructured":"Nucleophilic additions with MeMgBr and MeLi as the model sp3-carbon nucleophiles were also performed. All attempts however led either to a decomposition of the starting material or a mixture of many products that could not be identified except for the reaction ofT1with one equivalent of MeMgBr which gave a product of 1 4-addition."},{"key":"e_1_2_6_69_1","unstructured":"\u00a0"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b13300"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2010.04.062"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00906a017"},{"key":"e_1_2_6_73_1","unstructured":"\u00a0"},{"key":"e_1_2_6_74_2","first-page":"33","volume-title":"Ionic Reactions, in Frontier Orbitals and Organic Chemical Reactions","author":"Fleming I.","year":"1976"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01004a002"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01005a001"},{"key":"e_1_2_6_77_1","unstructured":"\u00a0"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601435"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102120"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol101720e"},{"key":"e_1_2_6_81_1","unstructured":"\u00a0"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-019-2515-1"},{"key":"e_1_2_6_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp5032702"},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp035848z"},{"key":"e_1_2_6_85_1","unstructured":"To support the view that these reactions occur under kinetic control the following crossover experiment suggested by a reviewer was carried out: The reaction ofA1with 10\u2005equivalents of ArMgBr (Table\u20051) was performed as usual but before quenching the reaction mixture was cooled to \u221278\u2009\u00b0C and 20\u2005equivalents ofp-tolylmagnesium bromide (TolMgBr) were added. Upon warming to room temperature and work-up no product of TolMgBr addition was observed onlyA4was formed."},{"key":"e_1_2_6_86_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19820650141"},{"key":"e_1_2_6_87_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90678-7"},{"key":"e_1_2_6_88_1","unstructured":"Variable-concentration experiments suggested by a reviewer revealed that the decrease of concentration fromc(ArMgBr)=10\u00d7c(A1)\u224880\u2005mm(reaching the solubility limit ofA1) by a factor of three leads to a decrease of the yield by approx. 20% while no other product is observed. The addition of LiCl (1.2\u2005equivalent with respect to ArMgBr) atc(ArMgBr)\u224880\u2005mmdoes not change the reaction outcome. These results indicate that in the rangec(ArMgBr)\u224826\u201380\u2005mm the aggregation effects of ArMgBr can be neglected. Typically the dione concentration was approx. 5\u2005mm."},{"key":"e_1_2_6_89_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c02197"},{"key":"e_1_2_6_90_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.5.31"},{"key":"e_1_2_6_91_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02769"},{"key":"e_1_2_6_92_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3sc50309g"},{"key":"e_1_2_6_93_1","unstructured":"\u00a0"},{"key":"e_1_2_6_94_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b00172"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301014d"},{"key":"e_1_2_6_96_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3sc53015a"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202016437","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202016437","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202016437","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,21]],"date-time":"2023-08-21T18:30:11Z","timestamp":1692642611000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202016437"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,4]]},"references-count":101,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2021,6,7]]}},"alternative-id":["10.1002\/anie.202016437"],"URL":"https:\/\/doi.org\/10.1002\/anie.202016437","archive":["Portico"],"relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv.13348049.v1","asserted-by":"object"}]},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,5,4]]},"assertion":[{"value":"2020-12-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-05-04","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}