Collect. Czech. Chem. Commun. 2002, 67, 471-478

An Unusual Transannular Rearrangement of a [2.2]Paracyclophane Derivative to Yield the First [6.2.2]Cyclophane

Andrew Peltera,*, Anne Harrison-Marchanda, Anderson Maxwellb, Baldwin Mootoob, Alicia Reida, Simon J. Colesc and Michael B. Hursthousec

a Department of Chemistry, University of Wales Swansea, Singleton Park, Swansea, SA2 8PP, U.K.
b Department of Chemistry, University of the West Indies, St Augustine, Trinidad & Tobago, West Indies
c EPSRC X-Ray Crystallography Service, Department of Chemistry, University of Southampton, Southampton, SO17 1BJ, U.K.


A unique transannular interaction in the [2.2]paracyclophane series that involves the disruption of an oxazoline on one of the aromatic rings by a ψ-geminal carboxyl group on the adjacent ring is described. The result is the linking of the two benzene rings by the formation of a new interannular ring containing an ester and a secondary amide linkage leading to the first [6.2.2]cyclophane.

Keywords: Transannular rearrangements; Cyclophanes; [2.2]Paracyclophane; [6.2.2]Cyclophane; Oxazoline ring opening; Interannular bridging.

References: 19 live references.