{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,20]],"date-time":"2026-09-20T13:37:50Z","timestamp":1789911470922,"version":"4.0.1"},"reference-count":27,"publisher":"Wiley","issue":"28","license":[{"start":{"date-parts":[[2015,6,8]],"date-time":"2015-06-08T00:00:00Z","timestamp":1433721600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Funded Access"},{"name":"Austrian Science Fund","award":["P19869-N19"],"award-info":[{"award-number":["P19869-N19"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2015,7,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The phosphonate\u2013phosphate rearrangement is an isomerisation of \u03b1\u2010hydroxyphosphonates bearing electron\u2010withdrawing substituents at the \u03b1\u2010carbon atom. We studied the stereochemical course of this rearrangement with respect to phosphorus. A set of four diastereomeric \u03b1\u2010hydroxyphosphonates was prepared by a Pudovik reaction from two diastereomeric cyclic phosphites. The hydroxyphosphonates were separated and rearranged with Et<jats:sub>3<\/jats:sub>N as base. In analogy to trichlorphon, which was the first reported compound undergoing this rearrangement. All four hydroxyphosphonates could be rearranged to 2,2\u2010dichlorovinyl phosphates. Single\u2010crystal X\u2010ray structure analyses of the \u03b1\u2010hydroxyphosphonates and the corresponding phosphates allowed us to show that the rearrangement proceeds with retention of configuration on the phosphorus atom.<\/jats:p>","DOI":"10.1002\/chem.201406661","type":"journal-article","created":{"date-parts":[[2015,6,10]],"date-time":"2015-06-10T19:42:31Z","timestamp":1433965351000},"page":"10200-10206","source":"Crossref","is-referenced-by-count":23,"title":["The Stereochemical Course of the \u03b1\u2010Hydroxyphosphonate\u2013Phosphate Rearrangement"],"prefix":"10.1002","volume":"21","author":[{"given":"Katharina","family":"Pallitsch","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander","family":"Roller","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Friedrich","family":"Hammerschmidt","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,6,8]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00351767"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01614a061"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/prac.19773190308"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01564a071"},{"key":"e_1_2_6_5_2","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1515\/znb-1969-0602","volume":"24","author":"Dedek W.","year":"1969","journal-title":"Z. Naturforsch. B"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00814152"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.198619861202"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-97876-0"},{"key":"e_1_2_6_9_2","first-page":"130","volume":"24","author":"Miyamoto J.","year":"1959","journal-title":"Bochu Kagaku"},{"key":"e_1_2_6_10_2","first-page":"19","volume":"2","author":"Brienne M. J.","year":"1978","journal-title":"Nouv. J. Chim."},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.03.103"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1984-30856"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob41574k"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00323a043"},{"key":"e_1_2_6_15_2","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.065.0006"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19830003019"},{"key":"e_1_2_6_18_2","unstructured":"ORTEP plots of all mentioned crystal structures can be found in the Supporting Information."},{"key":"e_1_2_6_19_2","unstructured":"A reviewer suggested decomposition of hydroxyphosphonates to give chloroform and (at room temperature) unstable formyl phosphonates as possible side reaction. We thank him very much for this suggestion. Unfortunately we did not find evidence for this hypothesis."},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197106871"},{"key":"e_1_2_6_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19710831706"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50044a004"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.198819880607"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja302072f"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1320039111"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00005-3"},{"key":"e_1_2_6_26_2","unstructured":"Later on it was discovered that by using CD2Cl2as solvent the reaction is completed within three hours at room temperature. The degree of conversion and the isolated yield are also higher in this case (around 70 and 60\u2009% respectively)."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201406661","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201406661","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:01:20Z","timestamp":1760299280000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201406661"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,6,8]]},"references-count":27,"journal-issue":{"issue":"28","published-print":{"date-parts":[[2015,7,6]]}},"alternative-id":["10.1002\/chem.201406661"],"URL":"https:\/\/doi.org\/10.1002\/chem.201406661","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,6,8]]}}}