Spontaneous Racemization and Epimerization Behavior in Solution of Chiral Nitroxides

Spontaneous Racemization and Epimerization Behavior in Solution of Chiral Nitroxides

Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations i...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2005-04, Vol.7 (9), p.1797-1800
Hauptverfasser: Ikuma, Naohiko, Tsue, Hirohito, Tsue, Naoko, Shimono, Satoshi, Uchida, Yoshiaki, Masaki, Kazuyoshi, Matsuoka, Nagahisa, Tamura, Rui
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Enantiomerically enriched samples of chiral cyclic nitroxides with a 4-hydroxyphenyl group on the stereogenic center bearing the NO radical group undergo unprecedented spontaneous racemization and/or epimerization in aprotic solvents, which can be well accounted for by the multistep equilibrations involving planar quinoid intermediates.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050401p