On the face of it, it would appear that you may have a claim for breach of contract if your right to private medical expenses is a part of your contract of employment and not a discretionary perk. By not submitting a formal request for funding through the proper channels, your employer has breached its contract with you. However, it would be your employer you would take any action against and not your boss personally. Employees must ALWAYS follow through their employer's own internal grievance procedure before pursuing a claim in an Employment Tribunal (not that I would advise going to an ET, very unpleasant, especially if you are still working with your employer). With the support of your union, follow the matter through the grievance procedure. If your employer upholds your grievance, you should be recompensed for your medical expenses.