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Die Oxidation zweier neuer 1,3‐Dihydroxyimidazolidine – Darstellung und Struktur von Nitronylnitroxid‐Radikalen
Author(s) -
Bätz Christof,
Amann Peter,
Deiseroth HansJörg,
Dulog Lothar
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.199419940715
Subject(s) - chemistry , radical , sodium periodate , nitroxide mediated radical polymerization , hydrogen bond , crystal structure , intermolecular force , molecule , polymer chemistry , single crystal , crystallography , medicinal chemistry , organic chemistry , polymer , radical polymerization , copolymer
The Oxidation of Two New 1,3‐Dihydroxyimidazolidines – Synthesis and Structure of Nitronyl Nitroxide Radicals The two new 1,3‐dihydroxyimidazolidines 3a and 3b were prepared by condensation of 4‐formylbenzoic acid ( 2a ) and sodium glyoxylate ( 2b ) with 2,3‐dimethyl‐2,3‐butanediylbis‐(hydroxylamine) sulfate ( 1 ). The 1,3‐dihydroxyimidazolidines were oxidized with sodium periodate in water to form nitronyl nitroxide radicals. Oxidation of the 1,3‐dihydroxyimidazolidine 3a yielded the new radical 4a , whereas the product obtained from the 1,3‐dihydroxyimidazolidine 3b was, due to decarboxylation, the unsubstituted radical 4c . The crystal structure of 4a was solved by single‐crystal X‐ray diffraction, showing the molecules to be arranged in zigzag chains as a consequence of intermolecular hydrogen bonds.