Abstract The synthesis of N-methyl-3-aza [10] paracyclophane is reported which represents the first example of this ring system being formed via an acyloin reaction. This 3-aza [10] paraeyclophane ring system behaves physiochemically inbetween the normal [9]-and [10] paracyclophane ring systems. Reductive desulfurization of N-methyl-3-aza [10] paracyclophane-6-ethylene thioketal in ethanol provides a small amount of the title ...