Heterocyclic Communications p. 25 - 28 (2007)
Update date:2022-08-11
Topics:
Winkeljohn, W. Rucks
Leggett-Robinson, Pamela
Peets, Monique R.
Strekowski, Lucjan
Vasquez, Pedro C.
Baumstark
The oxidation of 2-substituted pyridines and selected N-containing aromatic heterocycles by dimethyldioxirane (1) produced the corresponding N-oxides as the sole products, quantitatively in most cases. The second order rate constants for N-oxidation by 1 in dried acetone at 23°C were determined for a series of 2-substituted pyridines 2-10, quinolines 11-14 and isoquinolines 15,16. An excellent correlation of log k2 with Taft (σ*) constants was obtained for 2-substituted pyridines (R = Me, Et, Prn, Pr i, 3-pentyl) with the exception of the data for 2-f-butylpyridine. The results for the substituted quinolines and isoquinolines followed the same trends observed with the pyridines. Steric effects due to 2-substitution and periinteractions can substantially reduce reactivity. The results provide insights into the geometrical requirements for N-oxidation by dimethyldioxirane.
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