[3.3] Metacyclophane: a novel synthesis and a study of the structure through x-ray diffraction, molecular mechanics, and solution NMR analysis

MF Semmelhack, JJ Harrison, DC Young…

Index: Semmelhack,M.F.; Harrison,J.J.; Young,D.C. Journal of the American Chemical Society, 1985 , vol. 107, p. 7508

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Citation Number: 68

Abstract

Abstract: Coordination of 3-phenylpropionitrile with chromium hexacarbonyl followed by treatment of the resulting arenechromium complex with lithium diisopropylamide and then iodine produced 1, 12-dicyano [3.3] metacyclophane in a remarkable 84% yield. The process involves intermolecular nucleophilic addition to the coordinated arene, followed by cyclization of the dimer; iodine completes the addition/oxidation procedure for nucleophilic ...