Reactions of 2??chloro??2??(4??pyridyl) propane with nucleophiles. Substitution on tertiary carbon

H Feuer, JK Doty, N Kornblum

Index: Feuer, Henry; Doty,James K.; Kornblum, Nathan Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 783 - 787

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Abstract

Abstract The reaction of 2-chloro-2-(4-pyridyl) propane (2) with lithium 2-propanenitronate affords the C-alkylation product 2-nitro-3-(4-pyridyl)-2, 3-dimethylbutane (3), the Michael- adduct 2-nitro-2-methyl-4-(4-pyridyl) pentane (4), 4-isopropenylpyridine (5) and 2-(4-pyridyl)- 2-propanol (6). Of these four products, only the formation of 3 is suppressed when the reaction is performed in the presence of radical inhibitors. The reaction of compound 2 ...