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

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 …