114366-11-9Relevant academic research and scientific papers
Compounds with Bridgehead Nitrogen 52 -NMR Spectra and Stereochemistry of the 2-Alkylperhydroimidazolopyridines
Banting, Lee,Crabb, Trevor A.
, p. 696 - 706 (1987)
In contrast to perhydro-oxazolopyridine and perhydrothiazolopyridine, which adopt equilibria in CDCl3 solution at room temperature containing ca 70percent trans-fused conformers in equilibria with O- or S-inside cis-fused conformers, 2-alkylperhydroimidazolopyridines are found to adopt equilibria containing >98percent trans-fused conformers.Comparison of NMR parameters of 2-methylperhydroimidazolopyridine with those of the two isomers of 1,2-dimethylperhydroimidazolopyridine indicates an equilibrium for the former compound between the two trans-fused conformers, with ca 83percent of that conformation containing a transarrangement of nitrogen lone pairs of electrons.These observations are explained in terms of the generalized anomeric effect.KEY WORDS Perhydroimidazolopyridine Conformational equilibria 1H and 13C NMR
