Transformations of 4,9-dimethyl-2,3,7,8-tetra-azatetracyclo[7.3.1.0.4,1206,10]trideca-1,6-diene, a bishydrazone having two bridgehead double bonds

Abstract

Reduction of the anti-Bredt bishydrazone 4,9-dimethyl-2,3,7,8-tetra-azatetracyclo[7.3.1.0.^4,120^6,10]trideca-1,6-diene with lithium aluminium hydride–aluminium chloride or by catalytic hydrogenation gives the bishydrazine 1,6-dimethyl-2,3,7,8-tetra-azatetracyclo[7.3.1.0.^4,120^6,10]tridecane, but reaction with either lithium aluminium hydride or aluminium chloride gives dihydropyrazoles by ring cleavage.