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1.3‐Dipolare Cycloadditionen, XXXII. Kinetik der Additionen organischer Azide an CC‐Mehrfachbindungen
Abstract
Die IR‐spektrophotometrisch gemessenen Additionskonstanten des Phenylazids an 27 olefinische und 4 acetylenische Dipolarophile bei 25° liegen im Bereich von 7 Zehnerpotenzen; das Zusammenspiel elektronischer und sterischer Substituenteneffekte beim Dipolarophil wird diskutiert. — Kernsubstituierte Phenylazide befolgen in ihren Additionsgeschwindigkeiten die Hammett‐Gleichung, wobei der ρ‐Wert vom Dipolarophil abhängt: Maleinsäureanhydrid −1.1, N‐Phenyl‐maleinimid −0.8, Norbornen +0.88, Cyclopenten +0.9, 1‐Pyrrolidino‐cyclohexen +2.5. − Die für vier Azid‐Cycloadditionen ermittelten Aktivierungsentropien betragen −26 bis −36 Clausius. Die Additionskonstante des Phenylazids an Pyrrolidino‐cyclopenten hängt nur wenig von der Solvenspolarität ab. All diese Daten weisen auf eine Mehrzentren‐Cycloaddition der organischen Azide.
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Metadata
- Authors
- Huisgen, R., Szeimies, G., & Möbius, L.
- Venue
- Chemische Berichte
- Publisher
- Wiley
- Published
- 1967-08
- Volume
- 100
- Issue
- 8
- Pages
- 2494-2507
- ISSN
- 0009-2940 (ISSN-L)
- OpenAlex
- W2033945317
- Cited by
- 843
- References
- 0
- FWCI
- 4.13
- Type
- journal article
- Language
- en
- Open access
- closed
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- Huisgen, R., Szeimies, G., & Möbius, L. (1967). 1.3‐Dipolare Cycloadditionen, XXXII. Kinetik der Additionen organischer Azide an CC‐Mehrfachbindungen. Chemische Berichte. https://doi.org/10.1002/cber.19671000806
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