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 ...
