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- W2912373437 abstract "Sulfonates of exo-2-hydroxynorbornane-endo-2-carbonitrile (2c–e) were found to rearrange exothermally to give sulfonates of exo-2-hydroxynorbornane-1-carbonitrile (6c–e), solvolysis being a minor side reaction. In contrast, the analogous endo substrates (3c–e) afforded the rearranged alcohol 6a and tricyclo[2.2.1.02,6]heptane-1-carbonitrile (4) as the major products. We have not been able to trap 2-cyano-2-norbornyl cations by external nucleophiles or by internal 6,2-shifts of hydrogen or carbon. On the other hand, there is good evidence for the generation of 1-cyano-2-norbornyl cations from both 3d, e and 6e. The degenerate 6,2-H shift in these species has been uncovered by means of labeled or optically active precursors. The 1-CN substituent clearly promotes the 6,2-H shift relative to the parent 2-norbornyl cation, but is inferior to 1-C2F5. Ring expansion of a spiroannelated cyclopropane, involving a 6,2 shift of carbon, was also observed (25, 26 → 27, 28). Our data strongly suggest that 2-cyano-2-norbornyl cations are less stable than 1-cyano-2-norbornyl cations. The reaction rates of 2c versus 6c do not reflect the stability of the incipient carbocations, owing to the large difference in ground state energy." @default.
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- W2912373437 date "1993-03-01" @default.
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- W2912373437 title "Umlagerungen von 1- und 2-Cyan-2-norbornyl-Kationen" @default.
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- W2912373437 doi "https://doi.org/10.1002/cber.19931260326" @default.
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