Macrocycles containing bicyclophosphorane moieties [1]

The first stable macrocycles, 12–15, 16, 18, and 23, containing pentacovalent phosphorus have been obtained by an Atherton–Todd reaction between the bis(hydridobicyclophosphoranes) 3–7 and the corresponding binucleophile HO(CH2)2X(CH2)2OH. The tricyclic monophosphoranes 8–11 as well as the noncyclic derivative 20 have also been isolated. A pathway that accounts for the formation of all these compounds is proposed. The X-ray crystal study of two 16-membered rings, 14, 15, confirms the diequatorial placement of the macrocyclic frame on the trigonal bipyramidal phosphorus which retains the most favorable axial-equatorial-axial annelation of the bicyclic moiety. Comparison of these two molecular structures points out the effect of the nature of X on the conformation of the macrocycle.

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