Look at chemfinder it will show you the difference.
And here
https://www.thevespiary.org/rhodium/Rhodium/chemistry/yadontsay/ (https://www.thevespiary.org/rhodium/Rhodium/chemistry/yadontsay/)
You will see the difference between allyl benzenes and propenyl benzenes.
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no writeup, sorry. if i had one i would post it! my friend has other projects on his backburner, but maybe i can convince him to try that reaction again.
oxime formation is super easy: https://www.thevespiary.org/rhodium/Rhodium/chemistry/mdaoxime.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/mdaoxime.html)
MeOH was replaced with EtOH. all sizes where multiplied with 10. a tiny bit more of water was needed to dissolve the NaAc. product can take longer to crystalize (a day).
the al/hg reduction is basically your standard reduction with the following differences:
- use excess of Al (used 10x, next time will try using less)
- before adding the oxime, add some H2O and 4 eq. of AcOH
- let run for 12 hours.
- workup is a little bitchy (lots of unreacted Al). best would probably be to basify with lots of NaOH, wait until all Al has reacted, extract multiple times with alcohol and evaporate under vac (or would the water vapor carry away product?). then do your favorite A/B. filtering of the Al(OH)3 sludge did not work (it was sucked through!). what my friend did was messy: extract with toluene and wash with water. but the washing water separated in two phases(!), so he added some toluene and separated. you get the picture.
yields were an estimated 50% (back then he had no good scale!)
hth.