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- W2029606947 abstract "Access to spiro(bicyclo [2.2.1] heptane-2,1' -cycloprop-6-yl) derivatives was gained from the alkene spiro(bicyclo [2.2.1] hept-5-ene-2,1'-cyclopropane) via separation of positional isomers. Spiro(bicyclo [2.2.1]-2,1'-cycloprop-exo-6-yl) p-toluenesulphonate (10) and spiro(bicyclo [2.2.1] heptane-2,1'-cycloprop-exo-6-yl) trifluoroacetate were found to solvolyse faster than the analogous exo-2-norbornyl esters, as predicted by theory. Ion-pair recombination, with the formation of tricyclo [4.2.1.03,7] non-3-yl p-toluenesulphonate, accounts for previous failures to assess the true reactivity of 10. An intervening bridged carbocation (3), labelled with deuterium, was shown to achieve equivalence of C-1 and C-6 prior to ring expansion. The rate of the formal Wagner–Meerwein rearrangement is estimated to be of the order of molecular vibrations, thus supporting the symmetrical bridged structure of 3. Methyl substitution at C-6 was found to direct nucleophilic attack exclusively to the tertiary carbon, and ring expansion preferentially to the secondary carbon. An equilibrating pair of 6(1)-methylspiro(bicyclo [2.2.1] heptane-2,1′-cycloprop-6-yl) carbocations is thought to explain these observations most reasonably." @default.
- W2029606947 created "2016-06-24" @default.
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- W2029606947 date "1992-01-01" @default.
- W2029606947 modified "2023-09-27" @default.
- W2029606947 title "Generation and rearrangement of spirocyclopropane-substituted 2-norbornyl cations" @default.
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- W2029606947 doi "https://doi.org/10.1002/poc.610050104" @default.
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