Acid-catalyzed solvolysis: unusually rapid solvolysis of 3-fluoronortricyclene in CD3COOD – 0.1 M D2SO4 Academic Article uri icon

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abstract

  • 3-Fluoronortricyclene (1a) undergoes unusually facile solvolysis in CD3COOD – 0.1 M D2SO4 at 67 °C and yields 3-acetoxynortri-cyclene-d3 (1d) which ring-opens to a mixture of deuterated norbornyl diacetates. This result contrasts with the behaviour of 3-chloro- (1b) and 3-bromonortricyclene (1c) that undergo cleavage of the three-membered ring in CD3COOD – 0.1 M D2SO4. The estimated rate acceleration for solvolysis of alkyl fluorides in acid media is 107–108.

publication date

  • August 15, 1980