Abstract
AbstractThe stereoselectivity in the cyclodimerization of several six‐membered cyclic nitrones has been investigated. The configurational/conformational analysis of the dimers (i.e. perhydrodipyrido[1,2‐b;1′2′‐e]‐1,4,2,5‐dioxadiazines) has been carried out by NMR spectroscopy. The NMR spectra of the dimers at lower temperatures indicated the presence of either a single or two invertomer(s). The nitrogen inversion barriers are determined using complete line–shape analysis. The invertomer ratios have been used to estimate the relative energies associated with the cis and trans ring fusion in these tricycles. A mechanistic rationale for the observed stereochemistry of the dimerization process has been presented. Copyright © 2009 John Wiley & Sons, Ltd.
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