The Journal of Organic Chemistry
Article
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(83) The α-secondary EIE of 1.26 was reported in ref 82 for the
ADH-catalyzed conversion from benzyl alcohol to benzaldehyde (eq
3). For the model system, however, the direct hydride-transfer product
is the protonated aldehyde (eq 2). Therefore, the real EIE should be
equal to 1.26 times the EIE for the conversion from benzaldehyde to
its protonated form. The latter EIE was not seen in literature. Since the
process gains positive charge density at the benzylic carbon, the
corresponding EIE should be normal (>1, see refs 84 and 85). Thus,
this EIE of 1.26 is most likely a minimum estimation.
(84) Estimated from the reported β-secondaro EIE (1.28)82 for the
conversion from 2-propanol to acetone and that from acetone to the
protonated acetone (1.19).85
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