{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T17:41:54Z","timestamp":1790790114766,"version":"4.1.0"},"reference-count":49,"publisher":"American Chemical Society (ACS)","issue":"19","license":[{"start":{"date-parts":[[2017,9,28]],"date-time":"2017-09-28T00:00:00Z","timestamp":1506556800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R01 GM097243"],"award-info":[{"award-number":["R01 GM097243"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2017,10,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, none have been reported to work in more polar solvents. We report here that mixing ZnCl2 with TPPO precipitates a TPPO\u2013Zn complex in high yield in several common polar organic solvents. The solvent compatibility of this procedure and the reliability of the precipitation in the presence of polar functional groups were examined to show the utility and limitations of this method.<\/jats:p>","DOI":"10.1021\/acs.joc.7b00459","type":"journal-article","created":{"date-parts":[[2017,9,28]],"date-time":"2017-09-28T08:00:54Z","timestamp":1506585654000},"page":"9931-9936","source":"Crossref","is-referenced-by-count":111,"title":["Removal of Triphenylphosphine\nOxide by Precipitation\nwith Zinc Chloride in Polar Solvents"],"prefix":"10.1021","volume":"82","author":[{"given":"Donald C.","family":"Batesky","sequence":"first","affiliation":[{"name":"University of Rochester , , , , and","place":["Rochester, New York, United States, 14627-0216"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew J.","family":"Goldfogel","sequence":"additional","affiliation":[{"name":"University of Wisconsin , , , ,","place":["Madison, Wisconsin, United States, 53706"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9552-3378","authenticated-orcid":true,"given":"Daniel J.","family":"Weix","sequence":"additional","affiliation":[{"name":"University of Wisconsin , , , ,","place":["Madison, Wisconsin, United States, 53706"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2017,9,28]]},"reference":[{"key":"2026090218414489500_cit1","article-title":"Triphenylphosphine","volume-title":"Encyclopedia of Reagents for Organic Synthesis","author":"Cobb","year":"2001"},{"key":"2026090218414489500_cit2a","doi-asserted-by":"publisher","first-page":"739","DOI":"10.1039\/C5QO00016E","volume":"2","author":"Fletcher","year":"2015","journal-title":"Org. 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