{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,12]],"date-time":"2026-06-12T04:43:48Z","timestamp":1781239428408,"version":"3.54.1"},"reference-count":51,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2018,6,21]],"date-time":"2018-06-21T00:00:00Z","timestamp":1529539200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21732006, 21572212"],"award-info":[{"award-number":["21732006, 21572212"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21402181"],"award-info":[{"award-number":["21402181"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2018,7,20]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>\u03b3\u2010Lactones are an important class of fine chemical products and are widely used in perfumes, medicines, pesticides, dyes, and other fields. Herein, a new method for \u03b3\u2010lactones preparation based on ring contraction was developed. Starting from macrolides, W(OTf)<jats:sub>6<\/jats:sub> was used to catalyze the ring\u2010opening polymerization then depolymerization. The depolymerization step was not a common ring\u2010closing process, and the carbon number of the ring was reduced one by one by rearrangement to form the most thermodynamically stable five\u2010membered ring compounds. \u03b3\u2010Caprolactone (180\u2009\u00b0C for 10\u2005h) was obtained in a yield of 94\u2009% when [EMIM]OTf was used as the solvent, and the yield of isolated product was up to 85\u2009%. The interaction of various components and the reaction mechanism were studied by FTIR spectroscopy and <jats:sup>1<\/jats:sup>H\u2005NMR spectroscopy, respectively. Furthermore, \u03b3\u2010lactones could be produced when the substrate was extended to terminal hydroxyfatty acids. Unexpectedly, the catalyst was poisoned by 1\u2005equivalent of H<jats:sub>2<\/jats:sub>O added during the process and thus the yield decreased greatly. The reaction is green and simple, and proceeds in one pot with high atom economy (100\u2009% for macrolides and with water as the only byproduct for terminal hydroxyfatty acid), which provides a promising approach to synthesizing \u03b3\u2010lactones.<\/jats:p>","DOI":"10.1002\/cssc.201800587","type":"journal-article","created":{"date-parts":[[2018,5,24]],"date-time":"2018-05-24T05:35:00Z","timestamp":1527140100000},"page":"2332-2339","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["W(OTf)<sub>6<\/sub>\u2010Catalyzed Synthesis of \u03b3\u2010Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid"],"prefix":"10.1002","volume":"11","author":[{"given":"Zhong\u2010Yu","family":"Xie","sequence":"first","affiliation":[{"name":"Hefei National Laboratory for Physical Sciences at the Microscale, iChEM CAS Key Laboratory of Urban Pollutant Conversion Anhui Province Key Laboratory of Biomass Clean Energy Department of Chemistry University of Science and Technology of China  Hefei 230026 P.R. China"},{"name":"Nano Science and Technology Institute University of Science and Technology of China  Suzhou 215123 P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0272-1031","authenticated-orcid":false,"given":"Jin","family":"Deng","sequence":"additional","affiliation":[{"name":"Hefei National Laboratory for Physical Sciences at the Microscale, iChEM CAS Key Laboratory of Urban Pollutant Conversion Anhui Province Key Laboratory of Biomass Clean Energy Department of Chemistry University of Science and Technology of China  Hefei 230026 P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2282-4839","authenticated-orcid":false,"given":"Yao","family":"Fu","sequence":"additional","affiliation":[{"name":"Hefei National Laboratory for Physical Sciences at the Microscale, iChEM CAS Key Laboratory of Urban Pollutant Conversion Anhui Province Key Laboratory of Biomass Clean Energy Department of Chemistry University of Science and Technology of China  Hefei 230026 P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,6,21]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/B916853B"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00082"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1081\/SCC-200046534"},{"key":"e_1_2_7_5_1","unstructured":"\u00a0"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(98)00007-X"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00706-012-0921-3"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cattod.2016.01.028"},{"key":"e_1_2_7_9_1","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/b923907c"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/la101424a"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CY01374G"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2013.04.023"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA03435G"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10562-010-0368-2"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs400534x"},{"key":"e_1_2_7_18_1","unstructured":"\u00a0"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00955294"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00439"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcata.2007.09.013"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.04.112"},{"key":"e_1_2_7_23_1","unstructured":"\u00a0"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/c001226b"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma991580r"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b01569"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12039-015-0823-0"},{"key":"e_1_2_7_28_1","unstructured":"\u00a0"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00457"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00155"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201000201"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b00066"},{"key":"e_1_2_7_33_1","unstructured":"\u00a0"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201500907"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201000966"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC03125D"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201702073"},{"key":"e_1_2_7_38_1","unstructured":"\u00a0"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja411546r"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5EE03256C"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC01395G"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CY01149C"},{"key":"e_1_2_7_43_1","unstructured":"\u00a0"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b03470"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1732506"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm00043a006"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2004.11.043"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.3390\/ma7010527"},{"key":"e_1_2_7_49_1","unstructured":"\u00a0"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1141199"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106357j"}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcssc.201800587","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.201800587","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T16:34:32Z","timestamp":1760373272000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.201800587"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,6,21]]},"references-count":51,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2018,7,20]]}},"alternative-id":["10.1002\/cssc.201800587"],"URL":"https:\/\/doi.org\/10.1002\/cssc.201800587","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,6,21]]},"assertion":[{"value":"2018-03-19","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-06-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}