The typical structuring of old-for-new option exchanges generally will not satisfy the accommodation of option exchanges in the revised bump denial rules

Comments of Carr and Colden on the recent bump denial amendments include:

• Although specified property has been expanded by deeming shares to include options on shares (which sounds good), this provides no relief if a stock option exchange is structured in the usual manner: to benefit from the amendment, the parent must acquire the old target options in exchange for new parent options, so that the old options cannot simply be cancelled first.
• The inclusion in specified property of debt which was issued solely for money should extend to convertible debt.  However, the convertible debt might be determinable property (described in s. 88(1)(c.3)(ii)), given that specified property is not excluded from determinable property.
• In the context of the new rule which is intended to provide relief by permitting a person to be a specified person before the incorporation of the bump parent, such person should be considered (as an interpretative matter) to satisfy the proposed requirement of being related to the bump parent at the very moment of the incorporation of the bump parent notwithstanding that the bump parent would not yet have issued any shares.

Neal Armstrong.  Summaries of Brian R. Carr and Julie A. Colden, "The Bump Denial Rules Revisited", Canadian Tax Journal (2014) 62:1, 273-99 under ss. 88(1)(c.9), 88(1)(c.4)(ii) and 88(1)(c.2)(i).