An Acid Catalysed Intramolecular C–C Coupling Reaction of 8-halomethyl-16-methoxy[2.2]Metacyclophanes

Abstract

The hydrolysis of 8-bromomethyl[2.2]metacyclophane 1a with a methoxy group at the 16-position was carried out in an 80% aqueous dioxane solution by refluxing in the presence of Nafion-H (a solid perfluorinated resin sulfonic acid) as a catalyst. The reaction yielded the corresponding 8-hydroxymethyl[2.2]metacyclophane 3 and the intramolecular C–C coupling product 2 with a spiro skeleton.