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The reaction pathway was investigated, addition reactions with substituted thiols, hydrogen sulfide and protected cysteine were performed, and further modifications of the products were verified. The clean reaction proceeds by a radical chain process, which was confirmed by different deuterium labelling experiments. It shows high functional\u2010group tolerance, since halo\u2010, hydroxy\u2010, methoxy\u2010, carboxy\u2010, amino\u2010 and nitro\u2010substituted thiols could be added to <jats:bold>1<\/jats:bold> with few by\u2010products in 16\u201390\u2009% yield. Oxidation of the products allows tuning of the polarity and subsequent reactions of the products. The click\u2010type reaction proceeds even faster with selenols, as was shown in a proof of concept. Thiol addition to <jats:bold>1<\/jats:bold> offers a facile tool for surface modification, conjugation and tuning of hydrophilicity in bio\u2010 and medicinal chemistry.<\/jats:p>","DOI":"10.1002\/chem.201704105","type":"journal-article","created":{"date-parts":[[2017,10,16]],"date-time":"2017-10-16T16:06:29Z","timestamp":1508169989000},"page":"1373-1382","source":"Crossref","is-referenced-by-count":63,"title":["Alkyl and Aryl Thiol Addition to [1.1.1]Propellane: Scope and Limitations of a Fast Conjugation Reaction"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5122-7809","authenticated-orcid":false,"given":"Robin M.","family":"B\u00e4r","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Karlsruhe Institute of Technology (KIT)  Fritz-Haber-Weg 6 76131 Karlsruhe Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefan","family":"Kirschner","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Karlsruhe Institute of Technology (KIT)  Fritz-Haber-Weg 6 76131 Karlsruhe Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Nieger","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Helsinki  P.O. 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