Won't work, speaking from experience! We have a loft type upstairs bedroom. I installed a window type A/C through the wall into a well vented attic space. The A/C would work for a while and then cool very little as the heat built up in the attic space. Natural ventilation will not carry the heat produced by the A/C unit away fast enough. I believe that if the attic space was vented with a thermostatically controlled power ventilator that this arrangement could work. I never got that far, we just quit using the AC. Also, you will need to make provisions for dealing with the condensate produced, as stated above.
Cheers
Steve