ArticleScience advances2024
Taming nonclassical carbocations to control small ring reactivity.
Article in Science advances, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Dimerisation of aryl-substituted bicyclobutanes (BCBs): revealing a new mode of 1,3-dipolar background reactivity.Chemical science · 2026Article
- Asymmetric Carbonium Ion Catalysis: The Intramolecular Hydroalkoxylation of Cyclopropanes.Journal of the American Chemical Society · 2026Article
- Formally Stereoretentive SJournal of the American Chemical Society · 2025Article
- Stereospecific molecular rearrangement via nucleophilic substitution at quaternary stereocentres in acyclic systems.Nature chemistry · 2025Article
- Synthesis of Stereodefined Polysubstituted Bicyclo[1.1.0]butanes.Journal of the American Chemical Society · 2024Article
- Catalyst and Medium Control over Rebound Pathways in Manganese-Catalyzed Methylenic C-H Bond Oxidation.Journal of the American Chemical Society · 2024Article
- Highly Diastereoselective Preparation of Tertiary Alkyl Isonitriles by Stereoinvertive Nucleophilic Substitution at a Nonclassical Carbocation.Organic letters · 2023Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Prediction of the outcome of ring opening of small organic rings under cationic conditions can be challenging due to the intermediacy of nonclassical carbocations. For example, the solvolysis of cyclobutyl or cyclopropylmethyl derivatives generates up to four products on nucleophilic capture or elimination via cyclopropylcarbinyl and bicyclobutonium ions. Here, we show that such reaction outcomes can be controlled by subtle changes to the structure of nonclassical carbocation. Using bicyclo[1.1.0]butanes as cation precursors, the regio- and stereochemistry of ring opening is shown to depend on the degree and nature of the substituents on the cationic intermediates. Reaction outcomes are rationalized using computational models, resulting in a flowchart to predict product formation from a given cation precursor.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.