Reduced-symmetry deep-cavity cavitands

The syntheses of reduced-symmetry deep-cavity cavitands by two-stage stereoselective bridging with substituted benzal bromides is reported. Conditions for the optimal formation of the trisbridged derivatives were readily established. However, it was not possible to determine conditions which selectively promoted formation of either one of the two bisbridged species, or the monobridged compound, above the other products. A comparison of yields for A/B bisbridged derivatives verses A/C bisbridged derivatives may indicate that the one-pot formation of deep-cavity cavitands occurs primarily through the former species.