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Upon activation, neighboring\u2010group participation of the alkyne generates a nonclassical cyclopropylidenemethyl cation. The transformation provides access to densely\u2010substituted tertiary homopropargyl fluorides with broad functional\u2010group tolerance and efficient chirality transfer from enantioenriched alcohols. Computational studies support the involvement of the nonclassical cationic intermediate. The calculations further indicate that alkyne\u2010derived nonclassical cations are less stabilized than their alkene analogues.<\/jats:p>","DOI":"10.1002\/chem.71742","type":"journal-article","created":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T03:25:45Z","timestamp":1790825145000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Alkyne\u2010Assisted Stereospecific Skeletal Rearrangement via Nonclassical Carbocations"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-4197-8523","authenticated-orcid":false,"given":"Rajan Kumar","family":"Kharwar","sequence":"first","affiliation":[{"name":"Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis Technion\u2010Israel Institute of Technology  Haifa Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-9083-4131","authenticated-orcid":false,"given":"Kaushalendra","family":"Patel","sequence":"additional","affiliation":[{"name":"Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis Technion\u2010Israel Institute of Technology  Haifa Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-3340-7920","authenticated-orcid":false,"given":"Noam","family":"Orbach","sequence":"additional","affiliation":[{"name":"Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis Technion\u2010Israel Institute of Technology  Haifa Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9154-2320","authenticated-orcid":false,"given":"Ilan","family":"Marek","sequence":"additional","affiliation":[{"name":"Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis Technion\u2010Israel Institute of Technology  Haifa Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,30]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01176a536"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01150a029"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00009a003"},{"key":"e_1_2_10_5_1","doi-asserted-by":"crossref","DOI":"10.1007\/978-1-4613-4118-5","volume-title":"The Nonclassical Ion Problem","author":"Brown H. 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