On the alcohol- and water-catalyzed tautomerization of vitamins K1- and K2-derived quinone methide intermediates.

@article{Swartz2004OnTA,
  title={On the alcohol- and water-catalyzed tautomerization of vitamins K1- and K2-derived quinone methide intermediates.},
  author={Angela M Swartz and M Richard Barra and Donna Kuntz},
  journal={The Journal of organic chemistry},
  year={2004},
  volume={69 9},
  pages={
          3198-201
        }
}
Rates of conversion of 1,3-quinone methides into the corresponding 1,2-quinone methide tautomers, formed upon laser-flash excitation of vitamins K(1) and K(2) in CH(3)CN solutions, were determined in the presence of hydroxylic solvents (ROH; R = H, alkyl). In all cases, the tautomerization process is accelerated in the presence of ROH, and the corresponding observed rate constants show a cubed dependence on ROH concentration. This high-order dependency is attributed to a proton-relay transfer… CONTINUE READING
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