Abstract
Synthesis and reactivity analysis of the 1,2-dihydrocarbazol-4(3H)-one, and the N-methyl, N-tosyl and 2,2-dimethyl derivatives have been carried out. Molecular structures of the N-methyl and N-tosyl derivatives have been analyzed by X-ray diffraction. Crystals of the N-methyl derivative are monoclinic, space group P21/c,a=8.868(1),b=16.652(1),c=7.5440(4) Å, β=113.657(3). Crystals of the N-tosyl derivative are monoclinic, P21/c,a=12.0016(3),b=8.9178(2),c=16.0485(4) Å, β=104.372(2). An extended conjugation from the carbonyl group to the nitrogen atom and an envelope conformation for the common cyclohexenone fragment are evident in both cases. Oximation and Beckmann rearrangement, and etherification of the carbonyl group is reported.
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Rodríguez, J.G., del Valle, C., Esteban-Calderón, C. et al. Molecular structure and reactivity of the 1,2-dihydrocarbazol-4(3H)-one: X-ray crystal structure of N-methyl and N-(p-methylbenzenesulfonyl) derivatives. J Chem Crystallogr 25, 249–257 (1995). https://doi.org/10.1007/BF01665179
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DOI: https://doi.org/10.1007/BF01665179