Molecular Rearrangements

Chapter 11 Molecular Rearrangements J. M. Coxon, J. M. Coxon Department of Chemistry and Physics, University of Canterbury, Christchurch, New ZealandSearch for more papers by this author J. M. Coxon, J. M. Coxon Department of Chemistry and Physics, University of Canterbury, Christchurch, New ZealandSearch for more papers by this author Book Editor(s):Mark Moloney, Mark Moloney University of Oxford, Mansfield Road, Oxford, UK, OX1 3TA United KingdomSearch for more papers by this author First published: 15 March 2024 https://doi.org/10.1002/9781119716846.ch11Book Series:Organic Reaction Mechanisms Series AboutPDFPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShareShare a linkShare onEmailFacebookTwitterLinkedInRedditWechat Summary A blue-light-induced [2,3]-sigmatropic rearrangement of sulfonium ylides has been reported from donor/acceptor diazoalkanes and propargyl sulfides to give functionalized allenes and is considered to occur via singlet carbene intermediates. A mechanism, named maleimide-assisted rearrangement and cycloaromatization, has been reported to trigger the reactivity of acyclic enediynes by a cascade 1,3-proton transfer processes to enable acyclic enediynes to undergo cycloaromatization. Computational studies have been reported to gain insights into the potential energy surfaces of competing Lewis-acid catalyzed carbonyl-ene, Prins, and carbonyl-olefin metathesis reactions. Computational studies on the origin of enantioselectivity in the semipinacol rearrangement of vinylogous alpha-ketol cocatalyzed by a cinchona-based primary amine and Bronsted acids indicate the reaction proceeds via complexation, nucleophilic addition, dehydration, carbon atom migration, enamine–imine tautomerization, imine hydrolysis, and Walden inversion. References Orlowska , K. , Rybicka-Jasinska , K. , Krajewski , P. , and Gryko , D. , Org. Lett. , 22 , 1018 ( 2020 ). 10.1021/acs.orglett.9b04560 CASPubMedWeb of Science®Google Scholar Yuan , H. 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