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Communication | Regular issue | Vol 38, No. 10, 1994, pp.2147-2151
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6793
Macrocycle Formation via Arylnitrenium Ions: Possible Intramolecular Recognition

Rudolph A. Abramovitch* and Qing Shi

*Department of Chemistry, Clemson University, Clemson, SC 29631, U. S. A.


MMX calculations on 1-(4-nitrophenyl)-9-phenylnonane indicate that it has a global minimum energy conformation in which the aryl rings are within easy bonding distance, which is confirmed by 2D NOESY, ultraviolet and fluorescence spectroscopy; the corresponding arylnitrenium ion cyclizes to give mainly the 18-membered ring 4,4‘-nonamethylenediphenylamine, which results suggest that when electron-deficient and electron-rich aryl rings are joined by a long, flexible chain there exists an intramolecular attractive interaction between them that pre-orients them for cyclization.