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Chem."],"accepted":{"date-parts":[[2019,10,17]]},"abstract":"<jats:p><jats:italic>N<\/jats:italic>-Phenyl-<jats:italic>N<\/jats:italic>-(trifluoromethylsulfonyl)propiolamides react with triphenylphosphane in the presence of various active methylene compounds CH<jats:sub>2<\/jats:sub>XY in a 1:1:1 molar ratio to furnish 1-phosphonium-5-oxabetaines, Ph<jats:sub>3<\/jats:sub>P<jats:sup>+<\/jats:sup>\u2013C(R)=CH\u2013C(O<jats:sup>\u2013<\/jats:sup>)=CXY. These betaines are formed preferentially, but not exclusively, as <jats:italic>E<\/jats:italic>-diastereoisomers with respect to the vinylic double bond. In some cases, separation of the two diastereoisomers was achieved by fractionating crystallization. Structure determination by X-ray diffraction analysis revealed marked conformational differences around the CH\u2013C(O<jats:sup>\u2013<\/jats:sup>) single bond of <jats:italic>E<\/jats:italic> and <jats:italic>Z<\/jats:italic>-isomers and extended charge delocalization in the anionic part.<\/jats:p>","DOI":"10.3762\/bjoc.15.253","type":"journal-article","created":{"date-parts":[[2019,11,1]],"date-time":"2019-11-01T10:08:11Z","timestamp":1572602891000},"page":"2603-2611","source":"Crossref","is-referenced-by-count":3,"title":["1,5-Phosphonium betaines from <i>N<\/i>-triflylpropiolamides, triphenylphosphane, and active methylene compounds"],"prefix":"10.3762","volume":"15","author":[{"given":"Vito A","family":"Fiore","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chiara","family":"Freisler","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9289-4210","authenticated-orcid":false,"given":"Gerhard","family":"Maas","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"2086","published-online":{"date-parts":[[2019,11,1]]},"reference":[{"key":"ref1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00081"},{"key":"ref2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500593"},{"key":"ref3","doi-asserted-by":"publisher","DOI":"10.1039\/b717758e"},{"key":"ref4","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200404087"},{"key":"ref5","doi-asserted-by":"publisher","DOI":"10.2174\/138527208783330055"},{"key":"ref6","doi-asserted-by":"publisher","DOI":"10.1039\/c4nj01070a"},{"key":"ref7","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00390"},{"key":"ref8","doi-asserted-by":"publisher","DOI":"10.1039\/c8ob01343h"},{"key":"ref9","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4039(98)00811-9"},{"key":"ref10","doi-asserted-by":"publisher","DOI":"10.1080\/10426500210216"},{"key":"ref11","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4020(99)00220-3"},{"key":"ref12","doi-asserted-by":"publisher","DOI":"10.1016\/s0022-1139(99)00305-x"},{"key":"ref13","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2009.05.019"},{"key":"ref14","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21111514"},{"key":"ref15","doi-asserted-by":"publisher","DOI":"10.1021\/ja071990s"},{"key":"ref16","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902105"},{"key":"ref17","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201200400"},{"key":"ref18","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2019.05.027"},{"key":"ref19","doi-asserted-by":"publisher","DOI":"10.1515\/znb-2019-0100"},{"key":"ref20","doi-asserted-by":"publisher","DOI":"10.1007\/bf00816851"},{"key":"ref21","doi-asserted-by":"publisher","DOI":"10.1021\/jo00239a016"},{"key":"ref22","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4039(01)87289-0"},{"key":"ref23","doi-asserted-by":"publisher","DOI":"10.1055\/s-1993-22330"},{"key":"ref24","doi-asserted-by":"publisher","DOI":"10.1139\/v87-256"},{"key":"ref25","doi-asserted-by":"publisher","DOI":"10.1039\/c6cc01627h"},{"key":"ref26","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4039(01)96878-9"},{"key":"ref27","doi-asserted-by":"publisher","DOI":"10.1016\/s0040-4039(01)84699-2"},{"key":"ref28","doi-asserted-by":"publisher","DOI":"10.1039\/b109076n"},{"key":"ref29","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1270150110"},{"key":"ref30","doi-asserted-by":"crossref","first-page":"114","DOI":"10.3998\/ark.5550190.0008.311","author":"Espenlaub","year":"2007","journal-title":"ARKIVOC"},{"key":"ref31","doi-asserted-by":"publisher","DOI":"10.1021\/ja00844a003"}],"container-title":["Beilstein Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/15\/253","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/content\/pdf\/1860-5397-15-253.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/15\/253","content-type":"text\/html","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,6,24]],"date-time":"2021-06-24T08:24:27Z","timestamp":1624523067000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.beilstein-journals.org\/bjoc\/articles\/15\/253"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11,1]]},"references-count":31,"URL":"https:\/\/doi.org\/10.3762\/bjoc.15.253","archive":["Portico"],"relation":{},"ISSN":["1860-5397"],"issn-type":[{"type":"electronic","value":"1860-5397"}],"subject":[],"published":{"date-parts":[[2019,11,1]]}}}