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Supramolekulare Phosphorylierung kationischer Alkohole mit 3‐Arylindol‐4‐carboxamidin‐Struktur
Author(s) -
Reckenbeil Dieter,
Bats Jan W.,
Dürner Gerd,
Göbel Michael W.
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419941213
Subject(s) - chemistry , indole test , intramolecular force , protonation , cationic polymerization , ring (chemistry) , nucleophile , phosphorylation , stereochemistry , phosphoric acid , medicinal chemistry , ion , organic chemistry , biochemistry , catalysis
Supramolecular Phosphorylation of Cationic Alcohols with a 3‐Arylindole‐4‐carboxamidine Framework Recently we reported on the synthesis of 8‐phenylnaphthalene‐1‐carboxamidines equipped with nucleophilic side chains ( 1, 2 ). In the protonated state these compounds were able to coordinate phosphoric acid diesters as ion‐pair complexes and to react with them in a quasi‐intramolecular way. In comparison with noncharged alcohols high‐rate enhancements of phosphorylation could be achieved. Now we describe the synthesis of analogous amidinium alcohols constructed from a 3,4‐disubstituted indole framework. Due to the five‐membered ring of the indole the angle between the substituents of 4 and 5 is extended compared to the naphthalene derivatives 1 and 2 . As a result from this structural change a slight increase of the phosphorylation rate of 4 is observed.