{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T10:27:16Z","timestamp":1785407236907,"version":"3.56.0"},"reference-count":40,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2025,12,16]],"date-time":"2025-12-16T00:00:00Z","timestamp":1765843200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2025,12,16]],"date-time":"2025-12-16T00:00:00Z","timestamp":1765843200000},"content-version":"am","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2025,12,16]],"date-time":"2025-12-16T00:00:00Z","timestamp":1765843200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2025,11,27]]},"abstract":"<jats:p>\n                    In this paper, the mechanism of the hydroxy(tosyloxy)iodobenzene (HTIB)-mediated conversion of chalcones (\u03b1,\u03b2-unsaturated carbonyl compounds) to ditosyloxy ketones is investigated. Here, at \u03b2-carbon of the chalcone, an aryl group with a\n                    <jats:italic>para<\/jats:italic>\n                    -substituent is present. Our study focuses on investigating the effect of different nature of\n                    <jats:italic>para<\/jats:italic>\n                    -substituents on the reaction mechanism. The substituents considered in the study include -OCH\n                    <jats:sub>3<\/jats:sub>\n                    , -SCH\n                    <jats:sub>3<\/jats:sub>\n                    , -Cl and -NO\n                    <jats:sub>2<\/jats:sub>\n                    groups. For these chalcones, different possible pathways at various steps during the reaction are investigated leading to formation of \u03b1,\u03b2-ditosyloxy ketones and \u03b2,\u03b2-ditosyloxy ketones. It is found that the mechanism for the formation of \u03b1,\u03b2-ditosyloxy ketone involves only electrophilic addition of HTIB, and the mechanism is the same for all studied chalcones, irrespective of whether an electron-donating or electron-withdrawing substituent is present on the aryl ring. However, the detailed mechanism for the formation of \u03b2,\u03b2-ditosyloxy ketones is different and depends on the nature of the substituent. Broadly, the formation of \u03b2,\u03b2-ditosyloxy ketones involves electrophilic addition followed by 1,2-aryl migration. Our study shows that the presence of an electron-donating group on the migrating aryl ring favours the formation of \u03b2,\u03b2-ditosyloxy ketones while in case of electron-withdrawing groups, there are nearly equal chances of the formation of \u03b1,\u03b2-ditosyloxy ketones and \u03b2,\u03b2-ditosyloxy ketones.\n                  <\/jats:p>","DOI":"10.3762\/bjoc.21.208","type":"journal-article","created":{"date-parts":[[2025,12,16]],"date-time":"2025-12-16T13:48:47Z","timestamp":1765892927000},"page":"2703-2715","source":"Crossref","is-referenced-by-count":0,"title":["Mechanistic insights into hydroxy(tosyloxy)iodobenzene-mediated ditosyloxylation of chalcones: a DFT 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