Reaction of organic compounds under high temperature – dilute acid (HTDA) conditions. III. The perdeuteration of bicyclo[2.2.1]heptanes Academic Article uri icon

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abstract

  • The hydration of norbornene (1) and nortricyclane (2) under the high temperature and dilute acid (HTDA) conditions of aqueous acetic acid at 250 °C gives as products exo-2-norborneol, endo-2-norborneol, exo-2- and endo-2-norbornyl acetate, and a mixture of stereoisomeric dinorbornyl ethers 4. When the reactions are carried out in deuterated medium perdeuteration (>90% in one cycle) of the [2.2.1]-products is accomplished. Respectable overall yields (50–70%) of the products are obtained. Solvolysis of the products exo-norborneol, and endo-norbornyl acetate under HTDA(D) conditions also leads to perdeuterated 3a, 3b, 3c, 3d, and 4.

publication date

  • July 15, 1976