{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,19]],"date-time":"2026-10-19T17:10:44Z","timestamp":1792429844135,"version":"4.5.0"},"reference-count":108,"publisher":"Wiley","issue":"49","license":[{"start":{"date-parts":[[2018,3,5]],"date-time":"2018-03-05T00:00:00Z","timestamp":1520208000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2018,9,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The Al\/P\u2010based frustrated Lewis pair (FLP) Mes<jats:sub>2<\/jats:sub>P\u2212C(Al<jats:italic>t<\/jats:italic>Bu)<jats:sub>2<\/jats:sub>=C(H)Ph (<jats:bold>1<\/jats:bold>; Mes=mesityl) reacted as an efficient two\u2010electron reductant with benzil to afford a <jats:italic>cis<\/jats:italic>\u2010enediolate that was coordinated to the FLP through P\u2212O and Al\u2212O bonds and the formation of a seven\u2010membered heterocycle (<jats:bold>2<\/jats:bold>). The phosphorus atom is oxidised from +III to +V. Similar heterocycles (<jats:bold>3\u2009a<\/jats:bold> to <jats:bold>3\u2009f<\/jats:bold>) were formed if <jats:bold>1<\/jats:bold> was treated with various enones (acrolein, acrylate, acrylamide). The resulting enolates are bound to the FLP through P\u2212C and Al\u2212O bonds. Cyclopropenone gave an adduct (<jats:bold>4<\/jats:bold>) with the C=O bond coordinated by P and Al. Ynones gave a fascinating variety of different structures. 1,3\u2010Diphenylprop\u20102\u2010yn\u20101\u2010one afforded a remarkable allene\u2010type moiety with two cumulated C=C bonds (<jats:bold>5<\/jats:bold>); 3\u2010hexyn\u20102\u2010one yielded a ligand with two conjugated C=C bonds by C\u2212H bond activation at the carbonyl methyl group (<jats:bold>7<\/jats:bold>); and 4\u2010(trimethylsilyl)\u20103\u2010butyn\u20102\u2010one reacted by C\u2212H bond cleavage, formation of an enolate group with a terminal C=C bond, and shift of the proton to the P atom (<jats:bold>8<\/jats:bold>). The C\u2261C bond was not affected. Allene compound <jats:bold>5<\/jats:bold> rearranged at elevated temperature and in daylight through the formation of a tricyclic compound by C\u2212H bond activation and C\u2212C bond formation. DFT calculations on this unusual rearrangement suggest insertion of the central allene C atom into the C\u2212H bond of a methyl group and the intermediate formation of a C<jats:sub>3<\/jats:sub> ring.<\/jats:p>","DOI":"10.1002\/chem.201706089","type":"journal-article","created":{"date-parts":[[2018,1,16]],"date-time":"2018-01-16T08:18:59Z","timestamp":1516090739000},"page":"12856-12868","source":"Crossref","is-referenced-by-count":37,"title":["Reactions of an Aluminium\/Phosphorus Frustrated Lewis Pair (FLP) with \u03b1,\u03b2\u2010Unsaturated Carbonyl Compounds: FLPs as Efficient Two\u2010Electron Reductants with the Formation of Enolates, a <i>cis<\/i>\u2010Enediolate, and an Allene"],"prefix":"10.1002","volume":"24","author":[{"given":"Merten","family":"Lange","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Anorganische und Analytische Chemie Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstrasse 30 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonas C.","family":"Tendyck","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische und Analytische Chemie Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstrasse 30 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philipp","family":"Wegener","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische und Analytische Chemie Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstrasse 30 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Hepp","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische und Analytische Chemie Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstrasse 30 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ernst\u2010Ulrich","family":"W\u00fcrthwein","sequence":"additional","affiliation":[{"name":"Organisch-chemisches Institut and Center for, Multiscale Theory and Computation (CMTC) Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstrasse 40 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7178-5517","authenticated-orcid":false,"given":"Werner","family":"Uhl","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische und Analytische Chemie Westf\u00e4lische Wilhelms-Universit\u00e4t M\u00fcnster  Corrensstrasse 30 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,3,5]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","volume-title":"Frustrated Lewis Pairs","year":"2013"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903708"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200903708"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409800"},{"key":"e_1_2_6_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201409800"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1134230"},{"key":"e_1_2_6_6_1","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","first-page":"101","volume-title":"Frustrated Lewis Pairs, Vol. I and\u2005II, in Topics in Current Chemistry","author":"Uhl W.","year":"2013"},{"key":"e_1_2_6_8_2","unstructured":"M. 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