Title

Configurational and conformational mobility in a cross-conjugated derivative of 1,3-diketo-2-iminopropane

Document Type

Article

Date of Original Version

8-26-1999

Abstract

(Matrix presented) Mobility of configuration and conformation in the "push-pull" cross-conjugated derivative 1,3-diphenyl-2-(p-dimethylaminophenyl)iminopropane-1,3-dione has been investigated by NMR. The energetics of the thermal process that interconnects the syn-and anti-configurations of the imino group with the atropisomeric conformations of the skewed benzoyl groups are defined. It is proposed that a symmetric Y-delocalized transition state thermally interconnects the inversion of the imino configurations with the mobile interchange of the skewed benzoyl conformations. This connection is observable through a unique NMR window.

Publication Title

Organic Letters

Volume

1

Issue

4

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