In the picture, you can see the bridge whose end points are in para relation (for making the image clear).
Now, what my friend said is that there is no possibility of tautomerisation as there is no H to the right of =O and to the left of =O, on removing H, the bridge will be loaded(?!?).
But according to me, positive charge on the bridge end-points may be unstable as the bridge is out of the plane of the planar molecule and making it sp2 hybridized isn't a kind thing to do. But on removing H from the bridge end point (for tautomerisation), there will be negative charge on the bridge end point, which is perfectly normal.
So will it tautomerise or not?