Reduction by dissolving metals. Part XVIII. Metal–ammonia reductions of some bicyclo[2,2,2]octene derivatives: structural effects on double bond reduction and nitrile cleavage

Abstract

The reduction of the double bond in some bicyclo[2,2,2]octene derivatives by lithium in liquid ammonia is assisted by a methoxy- or a substituted amino-group at the bridgehead, and by an endo-carbinol group. Reductive removal of a cyano-group from the 2-position of bicyclo[2,2,2]octene or octane derivatives is similarly assisted by bridgehead methoxy- or amino-groups.