Ring expansion of substituted norbornadienes for the synthesis of mono- and disubstituted 2-azabicyclo[3.2.1]octadienes.
We have studied the conversion of substituted norbornadienes into a substituted 2-azabicyclo[3.2.1]octadiene system via reaction with toluenesulfonyl azide. We have found that both and mono- and disubstituted norbornadienes will undergo the cycloaddition/rearrangement sequence to provide the bicyclooctadiene ring system as a single regioisomer. The 2-azabicyclo[3.2.1]octane ring system can be prepared from the unsaturated 2-azabicyclo[3.2.1]octadiene ring system.
Emelda
Nova
N
Department of Chemistry & Biochemistry, Clippinger Laboratories, Ohio University, Athens, Ohio, 45701, USA.
Bergmeier
Stephen C
SC