Talk:Oppenauer oxidation
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Statement and formula error in the introduction
[edit]"The alcohol is oxidized with Aluminium-tert.-butylate in excess acetone" yet as the formula is written acetone appears to be the oxidant and the Al-compound (catalyst?) seems to be iso-propylate not tert-butylate —Preceding unsigned comment added by 90.239.69.12 (talk) 00:57, 9 March 2011 (UTC)
Image Error
[edit]The image provided depicts 3-nitrobenzaldehyde, yet the text refers to 2-nitrobenzaldehyde. This needs to be resolved. —Preceding unsigned comment added by 72.11.112.147 (talk) 18:06, 18 December 2008 (UTC)
Also, isoborneol shows a methyl group, looking at the paper referenced the structure provided concides with Wikipedia's image for isoborneol. As depicted it seems to be a tertiary alcohol being oxidizing into a ketone, which is actually a rare reaction. Fix the image. — Preceding unsigned comment added by 83.165.97.67 (talk) 19:32, 6 April 2020 (UTC)
Fixing steroid example
[edit]There's an example at the bottom of the page with a (3,10) steroid diol oxidized by the Oppenauer oxidation with 4-methylpiperidinone, and with reference 13 cited. There are two problems: [a] reference 13 (Synlett 2003, p. 570-572) has nothing to do with the steroid example shown, and has nothing to do with the Oppenaure oxidation at all. It's about chromium-catalyzed allylation. A careful reading shows nothing related to this topic at all, it appears to me that the reference is erroneous. [b] thus we don't know where the incorporated steroid example comes from, and if it's even valid, and if the reagents are correctly shown.
Using Scifinder Scholar, I did find examples of 3,10 steroid diols being oxidized by the Oppenaure oxidation method (a good paper is JOC 1994, 59, 5439-5444), and even for the substrate shown in this wikipedia page. However, this paper features the use of thallium(III) with the alcohol at position 10 as a directing group. So it's really not a good "general" example of the Oppenauer oxidation.
My change will consist of these things: [a] provide a better reference, for a more general use of the Oppenauer oxidation in steroids (Synth Commun 1972, 2(5), 323-325) [b] edit the text slightly [c] delete the old chemical drawing; provide an improved chemical drawing that matches the Synth Commun reference Mxa2 (talk) 22:49, 17 July 2013 (UTC)