Journal of Chemical Crystallography

, Volume 25, Issue 5, pp 249–257

Molecular structure and reactivity of the 1,2-dihydrocarbazol-4(3H)-one: X-ray crystal structure of N-methyl and N-(p-methylbenzenesulfonyl) derivatives

Authors

  • José Gonzalo Rodríguez
    • Departamento de Quimica, C1, Facultad de CienciasUniversidad Autonoma de Madrid
  • Celestina del Valle
    • Departamento de Quimica, C1, Facultad de CienciasUniversidad Autonoma de Madrid
  • Carmen Esteban-Calderón
    • Departmento de Rayos X, Instituto RocasolanoCSIC
  • Martín Martinez-Ripoll
    • Departmento de Rayos X, Instituto RocasolanoCSIC
Article

DOI: 10.1007/BF01665179

Cite this article as:
Rodríguez, J.G., del Valle, C., Esteban-Calderón, C. et al. J Chem Crystallogr (1995) 25: 249. doi:10.1007/BF01665179

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.

Key Words

Synthesisreactivitytetrahydrocarbazol-4-one

Copyright information

© Plenum Publishing Corporation 1995