>>11113209DA only really shows that benzyne can exist as an intermediate. A simpler solution would simply have been to substitute an activated ring with a halogen to generate the 2-subs product, then treat that to generate an amine. You would expect substitutions everywhere on the ring but you get it almost exclusively in the meta position relative to the original substituent, with the halogen released.
A better caging method is an intamolecular cyclization, as most other caging methods have stereoselective issues. At least this is what I think proves it without mapping electron density: Using an ortho attatched nucleophile, such as -CH2CH2CN, you can create an allylic compound in basic conditions to form an enolate. The enolate cyclizes on the ring to give (in our case a -four membered) n membered ring.
This can be isolated (this cyclization would not happen without that 'triple' bond system, especially in the geometry it is- with a third set of electrons in an sp2 orbital).
I will make these harder now I know youre here anon.
