ArticleThe Journal of organic chemistry2013
Enhanced reactivity in dioxirane C-H oxidations via strain release: a computational and experimental study.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 79 citations in OpenAlex.
- Designing Target-specific Data Sets for Regioselectivity Predictions on Complex Substrates.Journal of the American Chemical Society · 2025Article
- Tigliane Diterpenoids.Progress in the chemistry of organic natural products · 2024Review
- Radical and Cationic Pathways in C(Journal of the American Chemical Society · 2023Article
- Strategic application of C-H oxidation in natural product total synthesis.Nature reviews. Chemistry · 2023Review
- Article
- Strategy Evolution in a Skeletal Remodeling and C-H Functionalization-Based Synthesis of the Longiborneol Sesquiterpenoids.Journal of the American Chemical Society · 2022Article
- Ring Strain Energies of Three-Membered Homoatomic Inorganic Rings ElInorganic chemistry · 2022Article
- Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.Chemical reviews · 2022Review
- Total Synthesis and Late-Stage C-H Oxidations ofAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Total Synthesis and Late-Stage C-H Oxidations of ent-Trachylobane Natural Products.Angewandte Chemie (International ed. in English) · 2022Article
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- Late-Stage Diversification of Natural Products.ACS central science · 2020Review
- Molecule-Induced Radical Formation (MIRF) Reactions-A Reappraisal.Angewandte Chemie (International ed. in English) · 2020Review
- C(spOrganic chemistry frontiers : an international journal of organic chemistry · 2019Article
- Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.Journal of the American Chemical Society · 2018Article
- Aliphatic C-H Oxidations for Late-Stage Functionalization.Journal of the American Chemical Society · 2018Review
- The mechanism of directed Ni(ii)-catalyzed C-H iodination with molecular iodine.Chemical science · 2018Article
- Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(spChemical science · 2018Article
- Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.Chemical reviews · 2017Review
- Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.Journal of the American Chemical Society · 2017Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
The site selectivities and stereoselectivities of C-H oxidations of substituted cyclohexanes and trans-decalins by dimethyldioxirane (DMDO) were investigated computationally with quantum mechanical density functional theory (DFT). The multiconfiguration CASPT2 method was employed on model systems to establish the preferred mechanism and transition state geometry. The reaction pathway involving a rebound step is established to account for the retention of stereochemistry. The oxidation of sclareolide with dioxirane reagents is reported, including the oxidation by the in situ generated tBu-TFDO, a new dioxirane that better discriminates between C-H bonds on the basis of steric effects. The release of 1,3-diaxial strain in the transition state contributes to the site selectivity and enhanced equatorial C-H bond reactivity for tertiary C-H bonds, a result of the lowering of distortion energy. In addition to this strain release factor, steric and inductive effects contribute to the rates of C-H oxidation by dioxiranes.
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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.