The Vespiary

The Hive => Methods Discourse => Topic started by: Aurelius on November 21, 2002, 03:37:00 PM

Title: Decarboxylation
Post by: Aurelius on November 21, 2002, 03:37:00 PM: 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 (https://www.thevespiary.org/rhodium/Rhodium/chemistry/alpha-methylhydrocinnamic.html)
?
Title: Decarboxylation of alpha-methyl-cinnamic acid
Post by: Rhodium on November 21, 2002, 07:42:00 PM: 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 (https://www.thevespiary.org/rhodium/Rhodium/pdf/cinnamic.halodecarboxylation.pdf)
Title: wow
Post by: Aurelius on November 21, 2002, 09:14:00 PM: Hey Rhodium, it's horrible that you will never fully understand the gratitude aurelius has for you. thanks again!!! :)
Title: I'd be very glad if you could send your results ...
Post by: Rhodium on November 21, 2002, 09:33:00 PM: 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.
Title: Aurelius: Here you go with another article - ...
Post by: Rhodium on December 02, 2002, 11:58:00 PM: Aurelius: Here you go with another article -
https://www.thevespiary.org/rhodium/Rhodium/pdf/cinnamic.oxidative.carboxylation.pdf (https://www.thevespiary.org/rhodium/Rhodium/pdf/cinnamic.oxidative.carboxylation.pdf)
Title: cinnamic acid
Post by: pHarmacist on November 17, 2003, 02:49:00 AM: 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.
Title: more details?
Post by: Rhodium on November 17, 2003, 04:57:00 AM: Nice, but could you post the actual citation for that article? (Thieme's site includes a search engine if you lack any notes)
Title: Hmm..
Post by: pHarmacist on November 17, 2003, 07:50:00 AM: 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.
Title: Couldn't find it
Post by: Chromic on November 18, 2003, 09:41:00 AM: I did a quick search on thieme, but couldn't find it... looking for the keywords, nitrostyrene, nitric or microwave or combinations thereof.