Synthesis and Characterization of Chiral Guanidines und Guanidinium Salts Derived from 1-Phenylethylamine
Year: 2012
Type: article
Abstract: 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 C 3 symmetry, albeit unsymmetrical in the crystal - constitutes an intriguing structure with two rotamers present in solution.
Source: Zeitschrift für Naturforschung B
Institutions: University of Stuttgart, Hochschule Aalen
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $2,712
OpenAlex ID: W2321572609