Solvolysis of Substituted Nortricyclanes and Norbornenes at 250°

Solvolysis of nortricyclyl bromide (1a), nortricyclyl chloride (1b), nortricyclanol (1c), and 5- and 7-norbornenols (2b, 7) and exo-2,3-epoxybicyclo[2.2.1]heptane (11) in 10% v/v acetic acid – water at 250° yields 2-(cyclopentene)acetaldehyde (3), 3-(cyclopentene)acetaldehyde (4), 3-(cyclohexene)carboxaldehyde (5), norcamphor (6), and norbornanediols. In each case the diol concentration builds up then decreases as the conversion to 3, 4, 5, and 6 occurs. When the substrates 1a, b, and c, 2b, 7, 10a, and 11 are solvolyzed in deuterated medium, deuterium other than α to the carbornyl group is incorporated into the aldehydes and norcamphor.

Solvolysis of Substituted Nortricyclanes and Norbornenes at 250° Journal Articles