Crystal Structure of rac-4-Iodo-5-methoxy[2.2]metacylophane; A Rare Example of a Halogenated Metacyclophane with Planar Chirality

Abstract

A racemic mixture of planar chiral 4-iodo-5-methoxy[2.2]metacylophane ( 2 ) was synthesized by the low-temperature directed ortho aryl metalation of 5-methoxy[2.2]metacyclophane ( 1 ) and subsequent in situ reaction with iodine. The crystal structure was determined by the single-crystal X-ray diffraction method at 100 K. The compound crystallized in an orthorhombic system and was characterized as: Pca 2 1 , a = 13.5690(2), b = 14.2212(2), c = 7.5004(1)Å, Z = 4, V = 1447.33(4)Å 3 . The crystal structure was solved by direct methods and refined by full-matrix least-squares