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The C\u2261N triple bonds of nitriles insert into the P\u2212B bond of <jats:bold>2<\/jats:bold> with concomitant C\u2212B bond cleavage, whereas the C\u2261C bonds of phenylacetylenes react with <jats:bold>2<\/jats:bold> to form \u03bb<jats:sup>4<\/jats:sup>\u2010phosphabarrelenes. Even though <jats:bold>2<\/jats:bold> must formally be regarded as a classical Lewis adduct, the C\u2261N and C\u2261C activation processes observed (and the mild conditions under which they occur) are reminiscent of the reactivity of frustrated Lewis pairs. Indeed, NMR and computational studies give insight into the mechanism of the reactions and reveal the labile nature of the phosphorus\u2013boron bond in <jats:bold>2<\/jats:bold>, which is also suggested by detailed NMR spectroscopic studies on this compound. Nitrile insertion is thus preceded by ring opening of the bicycle of <jats:bold>2<\/jats:bold> through P\u2212B bond splitting with a low energy barrier. By contrast, the reaction with alkynes involves formation of a reactive zwitterionic methylphosphininium borate intermediate, which readily undergoes alkyne 1,4\u2010addition.<\/jats:p>","DOI":"10.1002\/chem.202000266","type":"journal-article","created":{"date-parts":[[2020,2,13]],"date-time":"2020-02-13T05:18:20Z","timestamp":1581571100000},"page":"7788-7800","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["A Phosphinine\u2010Derived 1\u2010Phospha\u20107\u2010Bora\u2010Norbornadiene: Frustrated Lewis Pair Type Activation of Triple Bonds"],"prefix":"10.1002","volume":"26","author":[{"given":"Julia","family":"Leitl","sequence":"first","affiliation":[{"name":"Institute of Inorganic Chemistry University of Regensburg  93040 Regensburg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4360-5838","authenticated-orcid":false,"given":"Andrew R.","family":"Jupp","sequence":"additional","affiliation":[{"name":"van \u2018t Hoff Institute for Molecular Sciences University of Amsterdam  Science Park 904, PO Box 94157 1090 GD Amsterdam The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Evi R. 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