Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation

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dc.contributor.authorMiah, M.A.J.
dc.contributor.authorSibi, M.P.
dc.contributor.authorChattopadhyay, S.
dc.contributor.authorFamiloni, O.B.
dc.contributor.authorSnieckus, V.
dc.date.accessioned2019-09-05T09:58:31Z
dc.date.available2019-09-05T09:58:31Z
dc.date.issued2017-09-20
dc.descriptionStaff publicationsen_US
dc.description.abstractThe directed ortho‐lithiation reactions of O‐aryl N,N‐dialkylcarbamates as well as O‐1‐naphthyl and O‐2‐naphthyl N,N‐dialkylcarbamates with sec‐butyllithium/tetramethylethylenediamine (sBuLi/TMEDA) followed by quenching with various electrophiles afford a range of polysubstituted aromatic compounds. If the solutions of the ortho‐lithiated carbamates are warmed to room temperature without the addition of external electrophiles, salicylamide and 1‐ and 2‐hydroxynaphthamide derivatives are formed through anionic ortho‐Fries rearrangements. The relative stabilities and reactivities of different O‐aryl N,N‐dialkylcarbamates were investigated. The lateral metalation of 2‐tolyl carbamates with lithium diisopropylamide (LDA) provides a route to benzo[b]furan‐2(3H)‐ones. Previously reported results are used in a comparison of seven O‐based directed metalation groups in reactions with several electrophiles. The described methodology is useful for the preparation of 1,2,3‐substituted aromatic compounds.en_US
dc.identifier.citationMiah, M. J., [Et...al] (2018). Directed ortho‐Metalation of O‐Aryl N, N‐Dialkylcarbamates: Methodology, Anionic ortho‐Fries Rearrangement, and Lateral Metalation. European Journal of Organic Chemistry, 2018(4), 440-446.en_US
dc.identifier.urihttps://ir.unilag.edu.ng/handle/123456789/5171
dc.language.isoen_USen_US
dc.publisherWiley Online Libraryen_US
dc.relation.ispartofseriesEuropean Journal of Organic Chemistry;Vol.2018(4)
dc.subjectResearch Subject Categories::NATURAL SCIENCES::Chemistry::Organic chemistry::Organic synthesisen_US
dc.subjectOrtho‐lithiation reactionsen_US
dc.subjectO‐1‐naphthyl and O‐2‐naphthyl N,N‐dialkylcarbamatesen_US
dc.subjectPolysubstituted aromatic compoundsen_US
dc.subject2‐tolyl carbamatesen_US
dc.titleDirected ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalationen_US
dc.typeArticleen_US
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