My itunes will not allow transfer of purchased items to my iphone4

As above, have brought in the heavy weights (my brother/apple expert) and even he is baffled!

Hey M.E.Hansen,
I would suggest that you select less items to sync onto your device. The bar at the bottom of iTunes when your iPhone is plugged in shows you how much space will be left on your phone AFTER the next sync, which is why it is not allowing you to sync:
iTunes 11 for Mac: Set up syncing for iPod, iPhone, or iPad
http://support.apple.com/kb/ph12113
The bar at the bottom of the window shows how much space will remain on your device after you sync.
Thanks for using the Apple Support Communities!
Cheers,
Braden

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