2-Lithio-3, 3-dimethyl-2-oxazolinyloxirane: Carbanion or Azaenolate? Structure, Configurational Stability, and Stereodynamics in Solution
V Capriati, S Florio, R Luisi, FM Perna…
Index: Perna, Filippo M.; Capriati, Vito; Florio, Saverio; Luisi, Renzo Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8351 - 8359
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Citation Number: 23
Abstract
Chemical studies have shown that, in ethereal solvents, oxiranyllithium Li-1 is configurationally unstable either on the macroscopic (Hoffmann's text) or microscopic time scale at low temperature (175 K). An optically pure sample of oxazolinyloxirane 1, once deprotonated, racemized within 1 min at− 130° C in THF/Et2O (3: 2)(t 1/2= 6.05 s); the application of the Eyring equation suggested a barrier to inversion for Li-1 of 8.8 kcal/mol ...
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