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Notizen. Addition von Carbonsäuren an (1S)-5,5-Dimethylbicyclo[2.2.1]hept-2-en (1984)

Kirmse, Wolfgang ; Brandt, Sigrid

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2524-2526

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ISSN: 0009-2940

Keywords: Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Addition of Carboxylic Acids to (1S)-5,5-Dimethylbicyclo[2.2.1]hept-2-eneProtonation of the title compound 5 induced Wagner-Meerwein rearrangement and 6,2(6,1)-hydride shifts, depending on the polarity of the acid (trifluoroacetic, acetic, and 2-ethylhexanoic acid). The optical purity of 5,5-dimethyl-2-norbornyl esters (7) exceeded that of 7,7-dimethyl-2-norbornyl esters (9). The results are interpreted in terms of asymmetric ion pairs which are tighter than those involved in deamination reactions.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19841170723

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