2-(2-Hydroxyaryl)cinnamic amides: a new class of axially chiral molecules (original) (raw)

Tetrahedron, 2006

Abstract

The syntheses of several differently substituted amides formally derived from a chiral amine, either E-2-(2-hydroxyphenyl)cinnamic acid or both E- and Z-2-(2-hydroxynaphthyl)cinnamic acid, are reported. These molecules display a restricted rotation about the C2–Caryl bond. The barriers to rotation about the C2–Caryl bond were measured by the dynamic 1H NMR and were found to vary between 11.8 and 24.5kcalmol−1, depending on

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