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Decarboxylation

Started by Aurelius, November 21, 2002, 03:37:00 PM

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Aurelius

What factors contribute to the ease of a decarboxylation by heat?  (as in Ritter's decarboxylation in high bp ketones)  how easy would it be to decarboxylate the product in the first step of

https://www.thevespiary.org/rhodium/Rhodium/chemistry/alpha-methylhydrocinnamic.html

    ?

Rhodium

alpha-methyl-cinnamic acid -> cis-propenylbenzene (Reflux, Quinoline, Copper powder)

J. Chem. Soc. Perkin Trans. 1, 10, 2491-2498 (1982)

alpha-methyl-cinnamic acid -> 2-bromo-propenylbenzene (NaBr, Oxone, Na2CO3(aq), 20°C)

https://www.thevespiary.org/rhodium/Rhodium/pdf/cinnamic.halodecarboxylation.pdf


Aurelius

Hey Rhodium, it's horrible that you will never fully understand the gratitude aurelius has for you.  thanks again!!! :)

Rhodium

I'd be very glad if you could send your results back to me with a full writeup.  :)  I don't lack literature and information, but I severely lack time and possibility to perform all the practical experiments I'd like to perform.


pHarmacist

Speaking about cinnamic acid derivatives, I've seen in Synthesis or Syntlett, route to nitrostyrenes from cinnamic acids + 15% HNO3 and T of -30 - 0 Celsius + MW from domestic owen, reaction gave excellent yields of nitrostyrenes.


Rhodium

Nice, but could you post the actual citation for that article? (Thieme's site includes a search engine if you lack any notes)

pHarmacist

I'll get it, I have the off-line copy at my mums place and I don't know more that that. However, at a bit higher temperatures 0 < T, the nitration takes place also on the ring, but at -30 it dosen't, at even higher temperatures the explosive picric acid (spellcheck) is a byproduct.


Chromic

I did a quick search on thieme, but couldn't find it... looking for the keywords, nitrostyrene, nitric or microwave or combinations thereof.