ArticleThe Journal of organic chemistry2019
Aryl Carbamates: Mechanisms of Orthosodiations and Snieckus-Fries Rearrangements.
Article in The Journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 24 citations in OpenAlex.
- Regioselective synthesis of aza-saccharinsChemical science · 2026Article
- The Versatile and StrategicChemical reviews · 2024Review
- Continuous Flow Preparation of Benzylic Sodium Organometallics.Angewandte Chemie (International ed. in English) · 2022Article
- Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis byJournal of the American Chemical Society · 2021Article
- (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.Angewandte Chemie (International ed. in English) · 2021Article
- Halogen-sodium exchange enables efficient access to organosodium compounds.Communications chemistry · 2021Article
- Preparation of Functionalized Aryl, Heteroaryl, and Benzylic Potassium Organometallics Using Potassium Diisopropylamide in Continuous Flow.Angewandte Chemie (International ed. in English) · 2020Article
- Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Aryl carbamates are orthometalated by sodium diisopropylamide (NaDA) in tetrahydrofuran. The resulting arylsodiums undergo Snieckus-Fries rearrangement to give orthoacylated phenols in good yield. The intermediate arylsodiums and resulting orthoacylated phenolates are suggested to be monomeric. The rate-limiting step in the two-step sequence depends on the steric demands of the carbamoyl moiety and the substituents in the meta position of the arene. Rate studies reveal a dominant disolvated-monomer-based orthometalation followed by a di- or trisolvated arylsodium monomer-based rearrangement. Kinetic evidence of a NaDA-catalyzed Snieckus-Fries rearrangement suggests the intermediacy of mixed trimers. Competitive halide eliminations to form benzyne are also discussed.
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