ArticleAngewandte Chemie (International ed. in English)2015
Acceleration of acetal hydrolysis by remote alkoxy groups: evidence for electrostatic effects on the formation of oxocarbenium ions.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
13 citing papers in PubMed, 27 citations in OpenAlex.
- Development and Mechanistic Studies of Oxidative Prins-Semipinacol Cyclization Reactions.Organic letters · 2026Article
- Umpolung Activation of Bicyclobutanes via N-Heterocyclic Carbene Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Toward Polymeric Room Temperature Acid Generators.ChemistryOpen · 2025Article
- Acetal Substitution Reactions: Stereoelectronic Effects, Conformational Analysis, Reactivity vs. Selectivity, and Neighboring-Group Participation.Synlett : accounts and rapid communications in synthetic organic chemistry · 2024Article
- Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides.The Journal of organic chemistry · 2022Article
- Ruthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism.Angewandte Chemie (International ed. in English) · 2021Article
- Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.Chemical reviews · 2020Article
- Stereoselective organocatalyzed glycosylations - thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings.Chemical science · 2019Article
- Chiral Pentacarboxycyclopentadiene-Based Brønsted Acid-Catalyzed Enantioselective Desymmetrization of Meso-Epoxides by 2-Mercaptobenzothiazoles.ACS omega · 2018Article
- Determination of the Influence of Side-Chain Conformation on Glycosylation Selectivity using Conformationally Restricted Donors.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates.Angewandte Chemie (International ed. in English) · 2016Article
- Absence of Stereodirecting Participation by 2-O-Alkoxycarbonylmethyl Ethers in 4,6-O-Benzylidene-Directed Mannosylation.The Journal of organic chemistry · 2015Article
- Participation of alkoxy groups in reactions of acetals: violation of the reactivity/selectivity principle in a Curtin-Hammett kinetic scenario.Angewandte Chemie (International ed. in English) · 2015Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
In contrast to observations with carbohydrates, experiments with 4-alkoxy-substituted acetals indicate that an alkoxy group can accelerate acetal hydrolysis by up to 20-fold compared to substrates without an alkoxy group. The acceleration of ionization in more flexible acetals can be up to 200-fold when compensated for inductive effects.
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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.