van Eis, Maurice J.; de Wolf, Willem H.; Bickelhaupt, Friedrich; Boese, Roland:

Structures and strain energies of small [n]metacyclophanes.

In: Perkin 2, (2000) ; Nr. 4, S. 793-801
ISSN: 1470-1820
Zeitschriftenaufsatz / Fach: Chemie
The structures and strain energies of various derivs. of [5]- and [6]metacyclophanes were computed by employing the d. functional method (ADF). They showed a good agreement with the few available x-ray crystal structures. The structure of 9,12-dichloro[6]metacyclophane was exptl. detd. at 200/233 K. Contrary to intuition, the incorporation of sp2-hybridized C atoms in the oligomethylene chain has a minor influence only on the structure and strain energy of these compds. Small metacyclophanes with potentially interesting interactions between unsatd. fragments in the bridge and the arom. ring or between 2 arom. rings, e.g. the so far elusive [1.1]metacyclophane, are realistic synthetic targets.