A novel rearrangement in a 1,3-bishomocubyl ring system

Alan P. Marchand, Pei-Wen Jin, J.L. Flippen-Anderson, R. Gilardi, Clifford George

Journal of the Chemical Society Chemical Communications · 1987 · 10 citations · 0 references

Concepts

Abstract

When treated with potassium ferricyanide–sodium nitrite in the presence of base, methyl 3,10-dinitropentacyclo-[5.3.0.02,5.O3,9.O4,8]decane-1-carboxylate undergoes an unusual skeletal rearrangement to afford methyl 3,9-dinitro-exo-10-methoxypentacyclo[5.3.0.02,5.03,9.04,8]decane-8-carboxylate whose structure was confirmed via single crystal X-ray crystallographic analysis.