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A phosphorus ylide bearing both P\uf8ffH and P\uf8ffF bonds was obtained by reaction of 2,4,6\u2010tris(2,4,6\u2010tri\u2010<jats:italic>tert<\/jats:italic>\u2010butylphenyl)\u20101,3,6\u2010triphosphafulvene with hydrogen tetrafluoroborate, and the structure was determined by X\u2010ray crystallography. Both P\uf8feC double bond and P<jats:sup>+<\/jats:sup>\uf8ffC<jats:sup>\u2212<\/jats:sup> zwitterionic character was indicated by the metric parameters. The isolated phosphorus ylide bearing a P\uf8ffH bond, [2,4\u2010bis(2,4,6\u2010tri\u2010<jats:italic>tert<\/jats:italic>\u2010butylphenyl)\u20101,3\u2010diphosphacyclopentadienylidene](2,4,6\u2010tri\u2010<jats:italic>tert<\/jats:italic>\u2010butylphenyl)phosphorane, showed no isomerization by H\u2010migration to the corresponding phosphinodiphospholes, probably due to the \u03c0\u2010accepting ability of the unsaturated PC bonds and aromaticity of the C<jats:sub>3<\/jats:sub>P<jats:sub>2<\/jats:sub> ring. The ylide structure and aromaticity of 2,4\u2010diphosphacyclopenta\u20102,4\u2010dienylidenephosphorane was characterized by theoretical calculations. In addition, the regioselective protonation of the lithiated phosphinodiphospholes generated from the 1,3,6\u2010triphosphafulvene is discussed.<\/jats:p>","DOI":"10.1002\/chem.200500374","type":"journal-article","created":{"date-parts":[[2005,7,29]],"date-time":"2005-07-29T07:22:53Z","timestamp":1122621773000},"page":"5960-5965","source":"Crossref","is-referenced-by-count":19,"title":["Synthesis of Phosphorus Ylides Bearing a P\uf8ffH Bond from a Kinetically Stabilized 1,3,6\u2010Triphosphafulvene"],"prefix":"10.1002","volume":"11","author":[{"given":"Shigekazu","family":"Ito","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hideaki","family":"Miyake","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masaaki","family":"Yoshifuji","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tibor","family":"H\u00f6ltzl","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tam\u00e1s","family":"Veszpr\u00e9mi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2005,9,26]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.210.4470.600"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19560890539"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19535800107"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19190020164"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527613908"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(80)80021-9"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19931050833"},{"key":"e_1_2_6_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199311671"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020916)114:18<3515::AID-ANGE3515>3.0.CO;2-D"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20021004)41:19<3668::AID-ANIE3668>3.0.CO;2-U"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01558a016"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01580a017"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00800a002"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000804)112:15<2892::AID-ANGE2892>3.0.CO;2-O"},{"key":"e_1_2_6_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000804)39:15<2781::AID-ANIE2781>3.0.CO;2-5"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-46100-0_3"},{"key":"e_1_2_6_14_2","volume-title":"Phosphorus: The Carbon Copy","author":"Dillon K. 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