Preparation of a series of 3- and 6-substituted 1,2,3,4-tetra- and 1,2,3,4,4a,9a-hexa-hydrocarbazoles

Abstract

A number of 3- and 6-substituted N-methyl-1,2,3,4,4a,9a-hexahydrocarbazoles, geometry syn,cis and cis respectively, have been prepared and characterised; the system has been designed as suitable for use in an examination of the transmission of substituent effects. The hexahydrocarbazoles are generally prepared by hydrogenation in strongly acidic solution of the corresponding 1,2,3,4-tetrahydrocarbazoles. The substituents are: 3-CO₂H, CH₂OH, CH₂OMe, CH₂OTs, CH₂CN, and CH₂Cl; and 6-CO₂Et, CH₂OH, CH₂OMe, CH₂CN, and CMe₂CN.