N-methylation of etioporphyrin I and octaalkyl-5-azaporphyrins : X-ray structure of trans-Na,Nb-dimethyletioporphyrin I triiodide |
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| Authors: | Ajita M Abeysekera Ronald Grigg Jadwiga Trocha-Grimshaw Kim Henrick |
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| Institution: | Department of Chemistry, Queen''s University, Belfast BT9 5AG, Northern Ireland;Chemistry Department, Polytechnic of North London, Holloway, London N7 8DB, England |
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| Abstract: | Improved procedures are reported for the preparation of mono-, di- and tri-N-methyl-etioporphyrin I. Demethylation of Na, Nb, Nc-trimethyletioporphyrin I under acidic, basic or thermal conditions gives Na, Nb-dimethyl etioporphyrin I. N-Methylation of octaalkyl-5-azaporphyrins leads, in general, to mixtures of the isomeric mono-, di- and tri-N-alkylated 5-azaporphyrins. An X-ray crystal structure of Na,Nb-dimethyl etioporphyrin I triiodide confirms the trans arrangement of the N-Me groups. The two N-methylated pyrrole rings are twisted 27° to each other. |
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