Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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.

Abstract

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.