Reaction of organic compounds under high temperature – dilute acid (HTDA) conditions. II. The hydration–exchange of norbornadiene and benzonorbornadiene in aqueous acetic acid at 250 °C

Abstract

The hydration of norbornadiene (1) under the HTDA conditions of aqueous acetic acid at 250 °C gives via norbornanediols and norbornenols as intermediates, the sink-product aldehydes 3, 4, 5, and norcamphor (6). When the reaction is carried out in deuterated medium on the average, 2.5 atoms of deuterium are incorporated into each of the products. Hydration of benzonorbornadiene (2) at 250 °C gives the alcohols 40 and 41 and the acetates 42a and 42b as products. When the hydration is carried out in deuterated medium, while only one atom of deuterium is incorporated into the [2.2.1]-framework, exchange of the aromatic moiety proceeds to completion.