ReviewOrganic & biomolecular chemistry2019
Allylic azides: synthesis, reactivity, and the Winstein rearrangement.
Review in Organic & biomolecular chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Electrochemical Ferrier rearrangement of glycals in flow.Communications chemistry · 2026Article
- Experimental and DFT studies on the regioselective methanolysis of 5-azido-9-oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers.Beilstein journal of organic chemistry · 2026Article
- Engineering protein prenylation: an emerging tool for selective protein modification.Biochemical Society transactions · 2025Review
- The Enigma of Sponge-Derived Terpenoid Isothiocyanate-Thiocyanate Pairs: A Biosynthetic Proposal.Marine drugs · 2025Review
- Article
- Synthesis of Three-Dimensional Ring Fused Heterocycles by a Selective [4 + 2] Cycloaddition Between Bicyclic Thiazolo 2-Pyridones and Arynes.The Journal of organic chemistry · 2024Article
- Progress toward the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement.Organic letters · 2023Article
- Synthesis of a New α-Azidomethyl Styrene from Safrole via a Dearomative Rearrangement.Molbank · 2023Article
- Radical-Mediated Functionalization of Internal Alkenes: Synthesis of Multisubstituted Allylic and Homoallylic Azides.ACS organic & inorganic Au · 2022Article
- Alternative approaches utilizing click chemistry to develop next-generation analogs of solithromycin.European journal of medicinal chemistry · 2022Article
- Intramolecular amination via acid-catalyzed rearrangement of azides: a potent alternative to intermolecular direct electrophilic route.Journal of molecular modeling · 2021Article
- Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinatedChemical communications (Cambridge, England) · 2021Article
- Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.Journal of the American Chemical Society · 2021Article
- A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles.Tetrahedron letters · 2021Article
- A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles.The Journal of organic chemistry · 2020Article
- H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.Chemical science · 2020Article
- Divergent Mechanisms of the Banert Cascade with Propargyl Azides.The Journal of organic chemistry · 2020Article
- Insight into the factors controlling the equilibrium of allylic azides.RSC advances · 2020Article
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Abstract
Organic azides are useful synthetic intermediates, which demonstrate broad reactivity. Unlike most organic azides, allylic azides can spontaneously rearrange to form a mixture of isomers. This rearrangement has been named the Winstein rearrangement. Using allylic azides can result in low yields and azide racemization in some synthetic contexts due to the Winstein rearrangement. Effort has been made to understand the mechanism of the Winstein rearrangement and to take advantage of this process. Several guiding principles can be used to identify which azides will produce a mixture of isomers and which will resist rearrangement. Selective reaction conditions can be used to differentiate the azide isomers in a dynamic manner. This review covers all aspects of allylic azides including their synthesis, their reactivity, the mechanism of the Winstein rearrangement, and reactions that can selectively elaborate an azide isomer. This review covers the literature from Winstein's initial report to early 2019.
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