ArticleThe Journal of organic chemistry2016
Sequential Photochemistry of Dibenzo[a,e]dicyclopropa[c,g][8]annulene-1,6-dione: Selective Formation of Didehydrodibenzo[a,e][8]annulenes with Ultrafast SPAAC Reactivity.
Article in The Journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Synthesis of Macrocyclic Structures by Intramolecular Photoclick Reaction.Journal of the American Chemical Society · 2026Article
- Visible and near-infrared light-induced photoclick reactions.Nature reviews. Chemistry · 2024Review
- Advances in the Synthesis of Bioorthogonal Reagents: s-Tetrazines, 1,2,4-Triazines, Cyclooctynes, Heterocycloheptynes, and trans-Cyclooctenes.Topics in current chemistry (Cham) · 2024Review
- Multiconfigurational photodynamics simulations reveal the mechanism of photodecarbonylations of cyclopropenones in explicit aqueous environments.Chemical science · 2023Article
- Toward "CO in a Pill": Silica-Immobilized Organic CO Prodrugs for Studying the Feasibility of Systemic Delivery of CO viaMolecular pharmaceutics · 2023Article
- EnablingJournal of the American Chemical Society · 2021Article
- Bioorthogonal Reactions of Triarylphosphines and Related Analogues.Chemical reviews · 2021Review
- Light-Triggered Click Chemistry.Chemical reviews · 2021Review
- Photoclick Chemistry: A Bright Idea.Chemical reviews · 2021Review
- Towards "CO in a pill": Pharmacokinetic studies of carbon monoxide prodrugs in mice.Journal of controlled release : official journal of the Controlled Release Society · 2020Article
- Live Monitoring of Strain-Promoted Azide Alkyne Cycloadditions in Complex Reaction Environments by Inline ATR-IR Spectroscopy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Photo-induced and Rapid Labeling of Tetrazine-Bearing Proteins via Cyclopropenone-Caged Bicyclononynes.Angewandte Chemie (International ed. in English) · 2019Review
- Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne-Azide Cycloaddition of Inorganic Azides.Bioconjugate chemistry · 2017Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
An order of magnitude difference in photoreactivity between bis- (photo-DIBOD, 1) and mono-cyclopropenone-caged dibenzocyclooctadiynes (MC-DIBOD, 5) allows for selective monodecarbonylation of 1. Alternatively, 5 is prepared by selective mono-cyclopropanation of dibenzo[a,e]cyclooctadiyne (DIBOD). MC-DIBOD (5) permits efficient sequential SPAAC cross-linking of azide-derivatized substrates. Cycloaddition to 5 converts an azide moiety into a photocaged form of triazole-fused dibenzo[a,e]cyclooctyne (3). While the azide reactivity of MC-DIBOD (5) and DIBOD is similar to that of other dibenzocyclooctynes, fusion of triazole to the dibenzocyclooctyne system in 3 results in a 3 orders of magnitude enhancement in SPAAC rates. In methanol, 3 reacts with butyl azide at an astonishing rate of 34 M
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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.