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Updated: May 10, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1-{(E)-[(2-Fluoro-5-nitro-phen-yl)imino]-meth-yl}naphthalen-2-ol
Alan R Kennedy1, Mehmet Akkurt, Antar A Abdelhamid
1Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland.
Abstract:
The title mol-ecule, C17H11FN2O3, is nearly planar [maximum deviation = 0.197 (1) Å] and the mol-ecular conformation is stabilized by an N-H⋯O hydrogen bond forming an S(6) ring motif. The H atom of the intra-molecular hydrogen bond was found to be disordered over two sites and thus both the hy-droxy and keto tautomers are simultaneously present in the solid. Refinement of the occupancy of this site suggests that the hy-droxy form is the major component [occupancy refined to 0.59 (3):0.41 (3)]. Bond lengths are also largely consistent with dominance of the hy-droxy form. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming layers parallel to (101). π-π stacking inter-actions [centroid-centroid distances = 3.5649 (9) and 3.7579 (9) Å] inter-connect these layers.
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