In confirming that interest on notes issued to pay dividends was non-deductible, as was interest on loans received from the shareholders to pay off the notes, the Directorate stated:
[I]t is the legal relationship between the parties that must be considered. In that regard, we understand that the notes were issued upon payment of the dividends. In our view, the interest-bearing debt was not used to pay the dividends.
… [T]here is no jurisprudence dealing with filling the hole in a situation such as the one under review. Since the concept of filling the hole is an exceptional circumstance for the purpose of allowing interest deductions, we cannot apply it in this case.