{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,22]],"date-time":"2026-04-22T10:48:35Z","timestamp":1776854915794,"version":"3.51.2"},"reference-count":53,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2020,4,22]],"date-time":"2020-04-22T00:00:00Z","timestamp":1587513600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/100010663","name":"H2020 European Research Council","doi-asserted-by":"publisher","award":["677749"],"award-info":[{"award-number":["677749"]}],"id":[{"id":"10.13039\/100010663","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Zeitschrift anorg allge chemie"],"published-print":{"date-parts":[[2020,7,15]]},"abstract":"<jats:p>The preparation and isolation of the metalated ylides [Cy<jats:sub>3<\/jats:sub>PCSO<jats:sub>2<\/jats:sub>Tol]M (<jats:bold><jats:sup>Cy<\/jats:sup>1\u2010M<\/jats:bold>) (with M = Li, Na, K) are reported. In contrast to its triphenylphosphonium analogue the synthesis of <jats:bold><jats:sup>Cy<\/jats:sup>1\u2010M<\/jats:bold> revealed to be less straight forward. Synthetic routes to the phosphonium salt precursor <jats:bold><jats:sup>Cy<\/jats:sup>1<\/jats:bold>\u2010<jats:bold>H<jats:sub>2<\/jats:sub><\/jats:bold> via different methods revealed to be unsuccessful or low\u2010yielding. However, nucleophilic attack of the ylide Cy<jats:sub>3<\/jats:sub>P = CH<jats:sub>2<\/jats:sub> at toluenesulfonyl fluoride under basic conditions proved to be a high\u2010yielding method directly leading to the ylide <jats:bold><jats:sup>Cy<\/jats:sup>1\u2010H<\/jats:bold>. Metalation to the yldiides was finally achieved with strong bases such as <jats:italic>n<\/jats:italic>BuLi, NaNH<jats:sub>2<\/jats:sub>, or BnK. In the solid state, the lithium compound forms a tetrameric structure consisting of a (C\u2013S\u2013O\u2013Li)<jats:sub>4<\/jats:sub> macrocycle, which incorporates an additional molecule of lithium iodide. The potassium compound forms a <jats:italic>C<\/jats:italic><jats:sub>4<\/jats:sub>\u2010symmetric structure with a (K<jats:sub>4<\/jats:sub>O<jats:sub>4<\/jats:sub>)<jats:sub>2<\/jats:sub> octahedral prism as central structural motif. Upon deprotonation the P\u2013C\u2013S linkage undergoes a remarkable contraction typical for metalated ylides.<\/jats:p>","DOI":"10.1002\/zaac.201900333","type":"journal-article","created":{"date-parts":[[2020,4,23]],"date-time":"2020-04-23T06:57:36Z","timestamp":1587625056000},"page":"835-841","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Synthesis, Isolation and Crystal Structures of the Metalated Ylides [Cy<sub>3<\/sub>P\u2010C\u2010SO<sub>2<\/sub>Tol]M (M = Li, Na, K)"],"prefix":"10.1002","volume":"646","author":[{"given":"Heidar","family":"Darmandeh","sequence":"first","affiliation":[{"name":"Chair of Inorganic Chemistry II Faculty of Chemistry and Biochemistry Ruhr University Bochum  Universit\u00e4tsstrasse 150 44780 Bochum Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thorsten","family":"Scherpf","sequence":"additional","affiliation":[{"name":"Chair of Inorganic Chemistry II Faculty of Chemistry and Biochemistry Ruhr University Bochum  Universit\u00e4tsstrasse 150 44780 Bochum Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kai\u2010Stephan","family":"Feichtner","sequence":"additional","affiliation":[{"name":"Chair of Inorganic Chemistry II Faculty of Chemistry and Biochemistry Ruhr University Bochum  Universit\u00e4tsstrasse 150 44780 Bochum Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher","family":"Schwarz","sequence":"additional","affiliation":[{"name":"Chair of Inorganic Chemistry II Faculty of Chemistry and Biochemistry Ruhr University Bochum  Universit\u00e4tsstrasse 150 44780 Bochum Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Viktoria H.","family":"Gessner","sequence":"additional","affiliation":[{"name":"Chair of Inorganic Chemistry II Faculty of Chemistry and Biochemistry Ruhr University Bochum  Universit\u00e4tsstrasse 150 44780 Bochum Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,4,22]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18940270152"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19190020164"},{"key":"e_1_2_6_2_3","first-page":"580","volume":"44","author":"Wittig G.","year":"1953","journal-title":"Liebig Ann. 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Eur. J."},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/recl.19720910106"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309399"},{"key":"e_1_2_6_17_1","unstructured":"Single crystals could only be obtained with LiI being present in the solution ofCy1\u2010Liin THF. Despite many affords we so far failed to grow crystals of pureCy1\u2010Li."},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900041"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr3002966"},{"key":"e_1_2_6_19_1","unstructured":"In the crystal the THF molecules on the rotational axis symmetrically occupy the space on top and below the octahedral prism and thus coordinate to all potassium atoms. These THF molecules are present with 95\u2009% occupancy. 5\u2009% of the space is filled by KI. Repeated crystallization gave the same structure yet always with poor quality due to heavily disordered cyclohexyl and solvent molecules."},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200801584"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767307043930"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024218"}],"container-title":["Zeitschrift f\u00fcr anorganische und allgemeine Chemie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fzaac.201900333","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/zaac.201900333","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/zaac.201900333","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/zaac.201900333","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,3]],"date-time":"2023-09-03T13:13:13Z","timestamp":1693746793000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/zaac.201900333"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,4,22]]},"references-count":53,"journal-issue":{"issue":"13","published-print":{"date-parts":[[2020,7,15]]}},"alternative-id":["10.1002\/zaac.201900333"],"URL":"https:\/\/doi.org\/10.1002\/zaac.201900333","archive":["Portico"],"relation":{},"ISSN":["0044-2313","1521-3749"],"issn-type":[{"value":"0044-2313","type":"print"},{"value":"1521-3749","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,4,22]]},"assertion":[{"value":"2019-12-12","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-04-22","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}