Lithiation of five-membered heteroaromatic compounds. The methyl substituted 1, 2-azoles, oxadiazoles, and thiadiazoles
RG Micetich
Index: Micetich,R.G. Canadian Journal of Chemistry, 1970 , vol. 48, p. 2006 - 2015
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Citation Number: 125
Abstract
The lithiation of various methyl substituted isoxazoles, isothiazoles, pyrazoles, oxadiazoles, and thiadiazoles using n-butyllithium has been studied. Three types of reactions, namely, lateral lithiation, ring cleavage, and addition of butyllithium to the ring, have been found. 3, 5- Dimethylisoxazole, 3-phenyl-5-methylisoxazole, 3, 4-dimethyl-1, 2, 5-oxadiazole, 2, 5- dimethyl-1, 3, 4-thiadiazole, 3-phenyl-5-methyl-1, 2, 4-oxadiazole, and 3, 5-dimethyl-1, 2, ...
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