Spontaneous Racemization and Epimerization Behavior in Solution of Chiral Nitroxides
Organic Letters2005Vol. 7(9), pp. 1797–1800
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Naohiko Ikuma, Hirohito Tsue, Naoko Tsue, Satoshi Shimono, Yoshiaki Uchida, Kazuyoshi Masaki, Nagahisa Matsuoka, Rui Tamura
Abstract
[reaction: see text] 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.
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