- AutorIn
- Klaus Banert
- Sandra Bochmann
- Andreas Ihle
- Oliver Plefka
- Florian Taubert
- Tina Walther
- Marcus Korb
- Tobias Rüffer
- Heinrich Lang
- Titel
- Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes
- Zitierfähige Url:
- https://nbn-resolving.org/urn:nbn:de:bsz:ch1-qucosa-152891
- Quellenangabe
- Banert, K.; Bochmann, S.; Ihle, A.; Plefka, O.; Taubert, F.; Walther, T.; Korb, M.; Rüffer, T.; Lang, H. Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes. Molecules 2014, 19, 14022-14035
- Abstract (EN)
- Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes to yield polycyclic products 3b–d, orthoesters 4a–c, ketones 5 or epoxides 6a,b, respectively. Treatment of bis(trimethylsilyl) acetylenedicarboxylate (1c) with cyclooctyne leads to the ketone 7 via retro-Brook rearrangement of the dipolar intermediate 2c. In all cases, the products are formed with perfect atom economy.
- Andere Ausgabe
- DOI: 10.3390/molecules190914022
- Link zur Originalpublikation in der Zeitschrift Molecules
Link: http://dx.doi.org/10.3390/molecules190914022 - Freie Schlagwörter (DE)
- Technische Universität Chemnitz, Publikationsfonds, Kaskadenreaktionen, Cyclopropene, Diels-Alder-Reaktionen, dipolare Zwischenstufen, Epoxide, Orthoester, Sauerstoffheterocyclen, Reaktionsmechanismen, Retro-Brook-Reaktionen, gespannte Verbindungen
- Freie Schlagwörter (EN)
- cascade reactions, cyclopropenes, Diels-Alder reactions, dipolar intermediates, epoxides, orthoesters, oxygen heterocycles, reaction mechanisms, retro-Brook reactions, strained compounds, Technische Universität Chemnitz, Publication funds
- Klassifikation (DDC)
- 540
- Normschlagwörter (GND)
- Epoxide, Ortho-Ester, Sauerstoffheterocyclen
- Herausgeber (Institution)
- Technische Universität Chemnitz
- Verlag
- MDPI AG, Basel
- URN Qucosa
- urn:nbn:de:bsz:ch1-qucosa-152891
- Veröffentlichungsdatum Qucosa
- 25.09.2014
- Dokumenttyp
- Artikel
- Sprache des Dokumentes
- Englisch