Kagutsuchi - 20-12-2015 at 03:43
I'm sorry if this has been discussed before. If there's a compound with multiple double or triple bonds, what will determine where the carbon chain
breaks up when oxidized by (Cr2O7)2- and H2SO4?
Etaoin Shrdlu - 20-12-2015 at 08:34
Both of them will react, generally speaking.
Boffis - 20-12-2015 at 13:08
It is possible to oxidize some functional groups on acetylenic compounds without oxidizing the triple bond. Somewhere I have a paper of the
preparation of Propynoic acid by this route and propynal from propargyl alcohol (propynol) using potassium dichromate is described at Org Synth.
(attached). This suggests that acetylenic bond can be fairly resistant to oxidation, I guess that it depends on what the other function groups are and
the frequency of double bonds.
Have you tried oxidizing sorbic acid, it has two adjacent ethylenic bond and is readily available/cheap so a good substrate for trials?
Attachment: CV4P0813.pdf (314kB)
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