1-AZABICYCLIC COMPOUNDS. 24. SELECTIVITY OF POSITION OF NITRATION OF 1,2-DIHYDROPYRROLIZINE, 5,6,7,8-TETRAHYDROPYRROCOLINE AND PYRROLE HOMOLOGS

Article abstract of DOI:10.1007/BF00479366

The selectivity of the position of nitration of 1-methylpyrrole, 1,2-dimethylpyrrole, 1,2-dihydropyrrolizine, and 5,6,7,8-tetrahydropyrrocoline was found.In contrast to the selectivity of substitution during nitration of their carbocyclic analogs, o-xylene, indane, and tetraline, the fraction of the α-nitro-isomer in the nitration products of 1,2-dimethylpyrrole is smaller than the fraction of α-nitro derivatives of 1,2-dihydropyrrolizine and 5,6,7,8-tetrahydropyrrocoline, and in the latter cases the isomers are almost equally distributed.During nitration of the above bicyclic pyrroles, the Mills-Nixon effect does not appreciably influence the selectivity of the position of the reaction.