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dc.contributor.authorMorrill, Charlotte
dc.contributor.authorGillespie, James E
dc.contributor.authorPhipps, Robert
dc.date.accessioned2022-06-15T23:30:42Z
dc.date.available2022-06-15T23:30:42Z
dc.date.issued2022-06-15
dc.identifier.issn1433-7851
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/338142
dc.description.abstractOrtho-sulfonyl anilines are important building blocks for a range of applications. We report the discovery of an aromatic rearrangement reaction of O-(arenesulfonyl)hydroxylamines which leads directly to ortho-sulfonyl anilines through formation of a new C-N bond with excellent levels of regiocontrol for the ortho position(s) over all others.  We establish that the rearrangement is proceeding through an intermolecular mechanism and propose that the regiocontrol observed is the result of attractive non-covalent interactions occurring during the C-N bond forming step.  Importantly, this method is complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that can be obtained and it is also applicable to O-(benzylsulfonyl) hydroxylamines.
dc.publisherWiley
dc.rightsAll Rights Reserved
dc.rights.urihttp://www.rioxx.net/licenses/all-rights-reserved
dc.titleAn Aminative Rearrangement of O-(Arenesulfonyl)hydroxylamines: Facile Access to ortho-Sulfonyl Anilines.
dc.typeArticle
dc.publisher.departmentDepartment of Chemistry
dc.date.updated2022-06-15T08:14:03Z
prism.publicationNameAngew Chem Int Ed Engl
dc.identifier.doi10.17863/CAM.85551
dcterms.dateAccepted2022-06-15
rioxxterms.versionofrecord10.1002/anie.202204025
rioxxterms.versionAM
dc.contributor.orcidPhipps, Robert [0000-0002-7383-5469]
dc.identifier.eissn1521-3773
rioxxterms.typeJournal Article/Review
pubs.funder-project-idRoyal Society (RGF/EA/180005)
pubs.funder-project-idEuropean Research Council (757381)
pubs.funder-project-idEngineering and Physical Sciences Research Council (EP/S03269X/1)
pubs.funder-project-idRoyal Society (URF\R\191003)
cam.issuedOnline2022-06-15
cam.orpheus.success2022-06-15 - Embargo set during processing via Fast-track
cam.depositDate2022-06-15
pubs.licence-identifierapollo-deposit-licence-2-1
pubs.licence-display-nameApollo Repository Deposit Licence Agreement
rioxxterms.freetoread.startdate2023-06-15


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