{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T18:11:42Z","timestamp":1760292702968,"version":"build-2065373602"},"reference-count":41,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2025,1,15]],"date-time":"2025-01-15T00:00:00Z","timestamp":1736899200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003977","name":"Israel Science Foundation","doi-asserted-by":"publisher","award":["2316\/19"],"award-info":[{"award-number":["2316\/19"]}],"id":[{"id":"10.13039\/501100003977","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The development of new protocols for stereospecific and stereoselective halogenation transformations by mild reaction conditions is a highly desirable research target for the chemical and pharmaceutical industries. Following the straightforward methodology for directly transforming a wide scope of alcohols to alkyl bromides and chlorides using substoichiometric amounts of thioureas and <jats:italic>N<\/jats:italic>\u2010halo succinimides (NXS) as a halogen source in a single step, we noticed that in apolar solvents bromination of chiral secondary alcohols did not produce the expected racemates. In this study, the stereochemical aspects of the bromination reaction were examined. Surprisingly, bromination of (\u00b1)\u2010<jats:italic>threo<\/jats:italic>\u2010 or (\u00b1)\u2010<jats:italic>erythro<\/jats:italic>\u20103\u2010phenyl\u20102\u2010butanols revealed a single diastereomeric brominated product with retention of configuration. The scope of these reactions was expanded on several \u03b2\u2010aryl alcohols. During these studies, an unexpected stereospecific 1,2\u2010migration of the phenyl group was shown to take place. The proposed mechanism of the 1,2\u2010phenyl migration involves the formation of a spiro[2,5]octadienyl radical, which is then attacked by a bromide radical at any of the two cyclopropyl positions anti to the phenyl position, leading to products that retain the stereoisomeric configuration of the starting material.<\/jats:p>","DOI":"10.1002\/chem.202403831","type":"journal-article","created":{"date-parts":[[2025,1,2]],"date-time":"2025-01-02T10:34:46Z","timestamp":1735814086000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Stereospecific Radical Bromination of <i>\u03b2<\/i>\u2010Aryl Alcohols with Thiourea Additives Through A Serendipitous Discovery of A 1,2\u2010Aryl Migration"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8649-6534","authenticated-orcid":false,"given":"Habib","family":"Assy","sequence":"first","affiliation":[{"name":"Department of Chemistry Ben-Gurion University of the Negev  Beer-Sheva 8410501 Israel"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Uttam K.","family":"Mishra","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ben-Gurion University of the Negev  Beer-Sheva 8410501 Israel"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-1445-199X","authenticated-orcid":false,"given":"Tom","family":"R\u00f6sler","sequence":"additional","affiliation":[{"name":"Department of Natural Sciences The Open University of Israel  Ra'anana 4353701 Israel."}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Raman","family":"Khurana","sequence":"additional","affiliation":[{"name":"Department of Natural Sciences The Open University of Israel  Ra'anana 4353701 Israel."}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1254-1149","authenticated-orcid":false,"given":"N. Gabriel","family":"Lemcoff","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ben-Gurion University of the Negev  Beer-Sheva 8410501 Israel"},{"name":"Ilse Katz Institute for Nanoscale Science and Technology Ben-Gurion University of the Negev  Beer-Sheva 8410501 Israel."}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1048-1947","authenticated-orcid":false,"given":"Ofer","family":"Reany","sequence":"additional","affiliation":[{"name":"Department of Natural Sciences The Open University of Israel  Ra'anana 4353701 Israel."}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,1,15]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.3390\/md14110206"},{"key":"e_1_2_8_2_1","first-page":"39","volume":"10","author":"Ravindranath B.","year":"1985","journal-title":"Perfumer Flavorist"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506388"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apsb.2023.11.021"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/np800651m"},{"key":"e_1_2_8_6_1","first-page":"5807","volume":"14","author":"Patil P.","year":"2023","journal-title":"Nat. Chem."},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201104638"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol5003972"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201604921"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01023"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja508799p"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-018-0042-1"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo3023439"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802472"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms6972"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2003.4"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02994B"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2020.11.022"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adq8029"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.4c03560"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4QO00077C"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c01431"},{"journal-title":"Research","year":"2022","author":"Rouh H.","key":"e_1_2_8_23_1"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.34133\/research.0163"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/agt2.543"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/B703488C"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/om000980w"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00075a064"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol3000712"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.9b07069"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo1004313"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199203421"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800004"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00386F"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202010839"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00467A"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.08.064"},{"key":"e_1_2_8_38_1","doi-asserted-by":"crossref","unstructured":"For1H NMR of12see: C. Rettenmeier H. Wadepohl L.\u2005H. GadeChe.-Eur. J. 2014 20 9657\u20139665.","DOI":"10.1002\/chem.201403243"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200400808"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200112)2001:23<4445::AID-EJOC4445>3.0.CO;2-U"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12010-010-8983-3"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202403831","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T17:39:12Z","timestamp":1760290752000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202403831"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,15]]},"references-count":41,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2025,4]]}},"alternative-id":["10.1002\/chem.202403831"],"URL":"https:\/\/doi.org\/10.1002\/chem.202403831","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2025,1,15]]},"assertion":[{"value":"2024-10-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-01-15","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202403831"}}