Article

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

  • José Gonzalo RodríguezAffiliated withDepartamento de Quimica, C1, Facultad de Ciencias, Universidad Autonoma de Madrid
  • , Celestina del ValleAffiliated withDepartamento de Quimica, C1, Facultad de Ciencias, Universidad Autonoma de Madrid
  • , Carmen Esteban-CalderónAffiliated withDepartmento de Rayos X, Instituto Rocasolano, CSIC
  • , Martín Martinez-RipollAffiliated withDepartmento de Rayos X, Instituto Rocasolano, CSIC

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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

Synthesis reactivity tetrahydrocarbazol-4-one