%A K Damodaran
%A SD Nielsen
%A SJ Geib
%A W Zhang
%A Y Lu
%A DP Curran
%J Journal of Organic Chemistry
%T Aryl-Csp<sup>3</sup> bond rotation barriers of 2-aryl perhydropyrrolo[3,4- c]pyrrole-1,3-diones
%X (Chemical Equation Presented) The static and dynamic features of 2-aryl perhydropyrrolo[3,4-c]pyrrole-1,3-diones bearing N-acyl substituents have been assessed with the aid of crystal structures and VT NMR spectra. Rotation barriers for the aryl-Csp3 bonds in these molecules show surprising variation. Amide-substituted derivatives and fused piperazinediones (six-membered fusion) exhibit very substantial barriers of 14-15 kcal/mol. Fused benzodiazepinediones (seven-membered fusion) have lower but still significant barriers (10 kcal/mol), while fused hydantoins (five-membered fusion) have barriers that are too low to measure by VT NMR (?10 kcal/mol). A rationale for the origin of the barriers is presented. ? 2009 American Chemical Society.
%N 15
%P 5481 - 5485
%V 74
%D 2009
%R 10.1021/jo901123c
%L pittir17333