Side Chain Hydroxylation of Aromatic Compounds by Fungi. Part 4. Influence of the para Substituent on Kinetic Isotope Effects During Benzylic Hydroxylation by Mortierella isabellina
The benzylic hydroxylation of a series of para-substituted toluenes by the fungus Mortierella isabellina has been studied by using CD3, CHD2, and CH2D methyl labelled substrates.Inter- and intramolecular primary and secondary deuterium kinetic isotope effect ratios have been determined: the intermolecular primary effects are maximal with strongly electron-withdrawing para substituents (R = CN and CF3), while the intramolecular primary effects are minimal for R = H but increase in instances where R is electron donating or withdrawing.These results are interpreted in terms of a dependence of the hydroxylation mechanism on the nature of the para substituent.
Holland, Herbert L.,Brown, Frances M.,Conn, Morgan
p. 1651 - 1655
(2007/10/02)
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