[swmmr1928]

As an alternative to DIAZONIUM SALTS FROM PHENYLAMINE, Could Diazonium Salt be synthesized from hydrazone and benzene?

By protonating hydrazone, it becomes an electrophile which is attacked by benzene.  Then remove some hydrogens and use those electrons to form the triple bond. 

Is this possible?

[swmmr1928]

Then remove some hydrogens and use those electrons to form the triple bond. 

Is this possible?

Rereading this, I remember the golden rule that hydrogens and carbons are never leaving groups.