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The paper analyses structural models for the evaluation of risky debt following H.E. LELAND [2], with an approach of optimal stopping problem (for instance cf. N. EL KAROUI [1]) and within a more general context: a dividend is paid to equity holders, moreover a different tax schedule is introduced, depending on the firm current value. Actually, an endogenous default boundary is introduced and a nonlinear convex tax schedule allowing for a possible switching in tax benefits. The aim is to find optimal capital structure such that the failure is delayed, meaning how to decrease the failure level VB, anyway preserving D debtholders and E equity holders’interests: for the firm VB is needed as low as possible, for the equity holder, an optimal equity is requested, finally an optimal coupon C is asked for the total value.
Keywords: corporate debt, optimal capital structure, default,