Ready formation of a Bredt compound, tricyclo[5,3,1,03,8]undec-2-ene. conformational preference leading to regiospecificity in a planar cis-elimination

Abstract
Dehydrobromination of 3,9-ethanobicyclo[3,3,1]-non-l-yl (tricyclo[5,3,1,03,8]undec-3-yl) bromide (I) with sodium amide in refluxing toluence gave 3,9-ethanobicyclo[3,3,1]non-1-ene (tricyclo[5,3,1,03,8]undec-2-ene)(II) in 52% yield.

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