Synthesis and Characterization of Chiral Guanidines und Guanidinium Salts Derived from 1-Phenylethylamine

Autor:	Amélie Castiglia, Thomas Orbegozo, Birgit Claasen, Wolfgang Frey, Hend Mohamed El Sehrawi, Volker Jäger, Dietrich Spitzner, Willi Kantlehner
Rok vydání:	2012
Předmět:	Steric effects Crystal chemistry.chemical_classification Tris chemistry.chemical_compound chemistry 1-Phenylethylamine Salt (chemistry) General Chemistry Crystal structure Conformational isomerism Medicinal chemistry Nmr data
Zdroj:	Zeitschrift für Naturforschung B. 67:337-346
ISSN:	1865-7117 0932-0776
DOI:	10.1515/znb-2012-0407
Popis:	The synthesis of two new chiral guanidines 5 and 12 and derived guanidinium salts 6, 11, 13 -15 with one and three N-(1-phenylethyl) substituents is described. In both cases, the well-precedented, reliable route via chloro-formamidines was taken. Since direct attachment of the N-methyl-N-(1- phenethyl)-amino group failed, the two-step protocol - introduction of the primary 1-phenethylamino group first followed by N-methylation - was employed. Crystal structures and NMR data reveal, that the sterically highly congested “tris” salt - with formal C3 symmetry, albeit unsymmetrical in the crystal - constitutes an intriguing structure with two rotamers present in solution.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8197f6599ddf08bd0ecb4227c159653a https://doi.org/10.1515/znb-2012-0407 Zobrazit plný text záznamu