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- W1436413986 abstract "This chapter describes the acid-catalyzed isomerization of bicyclic olefins including experimental and isomerizations in the C 8 H 12 series, C 9 H 14 , and C 10 H 16 . The low-temperature stability of bicyclo[2.2.1]heptane derivatives is well documented by the huge literature on liquid-phase norbornyl carbonium chemistry; under such conditions, no ring expansion is observed, but instead, multiple Wagner–Mecrwein rearrangements take place, preserving the bicyclo[2.2.l]heptane structure in the course of nucleophilic substitution or elimination reactions. However, if the norbornyl carbonium is brought to the proper temperature, passage to the more stable bicyclo[3.2.1]octane structure becomes possible. Lack of evidence for the reverse passage points to the lack of thermodynamic stability of the norbornyl structure even at low temperatures. The evolution of the systems with increasing temperature or reaction time indicates that bicyclo[3.2.1]octane structures, rather stable in the medium range of temperatures (160–200°) are irreversibly converted to bicyclo[3.3.0]octane isomers at higher temperatures (250°)." @default.
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- W1436413986 date "1969-01-01" @default.
- W1436413986 modified "2023-09-23" @default.
- W1436413986 title "Acid-Catalyzed Isomerization of Bicyclic Olefins" @default.
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- W1436413986 doi "https://doi.org/10.1016/s0360-0564(08)60273-4" @default.
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