Ring expansion of substituted norbornadienes for the synthesis of mono-and disubstituted 2-azabicyclo [3.2. 1] octadienes

N Emelda, SC Bergmeier

Index: Emelda, Nova; Bergmeier, Stephen C. Tetrahedron Letters, 2008 , vol. 49, # 37 p. 5363 - 5365

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Abstract

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 ...