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Approaches to Destabilized 7-Norbornyl Cations

Wolfgang Kirmse ; Ruhr-Universitat Bochum, Fakultat für Chemie, P.O.B. 102148, D-4630 Bochum, Germany
Sabine Schoen ; Ruhr-Universitat Bochum, Fakultat für Chemie, P.O.B. 102148, D-4630 Bochum, Germany

Puni tekst: engleski, pdf (35 MB) str. 551-566 preuzimanja: 131* citiraj
APA 6th Edition
Kirmse, W. i Schoen, S. (1992). Approaches to Destabilized 7-Norbornyl Cations. Croatica Chemica Acta, 65 (3), 551-566. Preuzeto s https://hrcak.srce.hr/137116
MLA 8th Edition
Kirmse, Wolfgang i Sabine Schoen. "Approaches to Destabilized 7-Norbornyl Cations." Croatica Chemica Acta, vol. 65, br. 3, 1992, str. 551-566. https://hrcak.srce.hr/137116. Citirano 07.03.2021.
Chicago 17th Edition
Kirmse, Wolfgang i Sabine Schoen. "Approaches to Destabilized 7-Norbornyl Cations." Croatica Chemica Acta 65, br. 3 (1992): 551-566. https://hrcak.srce.hr/137116
Harvard
Kirmse, W., i Schoen, S. (1992). 'Approaches to Destabilized 7-Norbornyl Cations', Croatica Chemica Acta, 65(3), str. 551-566. Preuzeto s: https://hrcak.srce.hr/137116 (Datum pristupa: 07.03.2021.)
Vancouver
Kirmse W, Schoen S. Approaches to Destabilized 7-Norbornyl Cations. Croatica Chemica Acta [Internet]. 1992 [pristupljeno 07.03.2021.];65(3):551-566. Dostupno na: https://hrcak.srce.hr/137116
IEEE
W. Kirmse i S. Schoen, "Approaches to Destabilized 7-Norbornyl Cations", Croatica Chemica Acta, vol.65, br. 3, str. 551-566, 1992. [Online]. Dostupno na: https://hrcak.srce.hr/137116. [Citirano: 07.03.2021.]

Sažetak
2-Oxo-7-norbornyl cations and l-eyano-7-norbornyl cations have been generated from various precursors, mostly derivatives of bicyclo[3.2.0]hep- tane. Whereas 2-bromobicyclo[3.2.0]heptan-3-one (17) solvolyzed exclusively with formation of 2-methoxybicyclo[3.2.0]heptan-3-ones (19,20), the analogous diazonium ion rearranged in part to give syn-7-methoxynorbornan-2-one (29). The epimeric 2-brosyloxybicyclo[3.2.0]heptane-2-carbonitriles (34,35) solvolyzed with predominant migration of C-7, yielding l-cyano-7-norbomyl derivatives without significant anti -*syn leakage. Similarly, the decomposition of 5-cyanobicyclo[3.2.0]heptane-2-diazonium ions (47) led to 7-hydroxynor- bornane-l-carbonitrile (38) in a stereospecific manner. Slightly lower stereoselectivity (ca 90%) was observed in solvolyses of labeled l-cyano-7-norbornyl triflate (39). While the stereochemical data conform with those of the parent system, the lack of bridge flipping (40242) points to graded destabilization of bridged and open ions.

Hrčak ID: 137116

URI
https://hrcak.srce.hr/137116

Posjeta: 271 *