Aromatic substitution. Part XXIII. Reaction of some 3-substituted pyridines with alkyl-lithium compounds
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 901-903
- https://doi.org/10.1039/j29690000901
Abstract
The reaction of methyl-, isopropyl-, and benzyl-lithium with pyridine and 3-picoline has been investigated quantitatively. Isomer ratios and total and partial rate factors have been determined. The selectivity is in the order benzyl-lithium phenyl-lithium > methyl-lithium > isopropyl-lithium. No activation of C-2 in 3-picoline was observed with the alkyl-lithium derivatives. The benzyl group substitutes at C-4 exclusively. Explanations for the observed data are given based on the reactivity and size of the attacking anions.Keywords
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