The 2-Norbornyl Cation via the Fragmentations of exo- and endo-2-Norbornyloxychlorocarbenes:  Distinction without Much Difference

The 2-Norbornyl Cation via the Fragmentations of exo- and endo-2-Norbornyloxychlorocarbenes:  Distinction without Much Difference

exo- and endo-2-norbornyloxychlorocarbenes (7) were generated photochemically from the corresponding diazirines (6). Both carbenes fragmented to [2-norbornyl cation (carbon monoxide) chloride] ion pairs in MeCN or 1,2-dichloroethane solutions. Products included exo-norbornyl chloride (8), endo-norbo...

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Veröffentlicht in:Journal of the American Chemical Society 2001-08, Vol.123 (33), p.8109-8116
Hauptverfasser: Moss, Robert A, Zheng, Fengmei, Sauers, Ronald R, Toscano, John P
Format: Artikel
Sprache:eng
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Zusammenfassung:exo- and endo-2-norbornyloxychlorocarbenes (7) were generated photochemically from the corresponding diazirines (6). Both carbenes fragmented to [2-norbornyl cation (carbon monoxide) chloride] ion pairs in MeCN or 1,2-dichloroethane solutions. Products included exo-norbornyl chloride (8), endo-norbornyl chloride (9), norbornene (10), and nortricyclene (11). Fragmentation activation energies were very low (
ISSN:0002-7863
1520-5126
DOI:10.1021/ja010598q