Premium
Chemie von α‐Aminonitrilen 22. Mitteilung Regioselektive Synthese und Kristallstruktur von Uroporphyrinogen‐(Typ I)‐octanitril
Author(s) -
Lehmann Christian,
Schweizer Bernd,
Leumann Christian,
Eschenmoser Albert
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800508
Subject(s) - chemistry , regioselectivity , crystal structure , stereochemistry , derivative (finance) , molecule , crystallography , organic chemistry , catalysis , financial economics , economics
Chemistry of α‐Aminonitriles. Regioselective Synthesis and Crystal Structure of Uroporphyrinogen (Type I) Octanitrile A regioselective synthesis of uroporphyrinogen‐octanitrile (type I) based on the strategy of multiple use of (dimethylmethylidene)ammonium iodide for stepwise regioselective functionalization of the pyrrole nucleus is described. This uroporphyrinogen derivative is remarkably stable and beautifully crystallizes in space group P 1 with one molecule per unit cell. The crystal structure of the compound shows interesting conformational characteristics which are interpreted to be caused by subtle stereoelectronic effects. The English Footnotes to Schemes 1‐3 and Figs. 1‐12 provide an extension of this summary.