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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Oropimente on August 20, 2019, 12:37:38 PM

Title: Catalytic reactions that improved existing reactions
Post by: Oropimente on August 20, 2019, 12:37:38 PM

So, I found this example of Reppe's [2+2+2+2] cycloaddition reaction as an example of using catalytic systems that improved the synthesis of a otherwise difficult compound in a thesis.

(https://i.ibb.co/xLKX1Bp/IMG-1339.jpg)
Reppe and coworkers, Justus Liebigs Ann. Chem. 1948, 560, 1, for the Ni reaction.

Are there another examples of reactions like this one? Like the synthesis of adamantane (https://en.wikipedia.org/wiki/Adamantane) from dicyclopentadiene, which is awesome. I'm asking because in our group we use that Reppe example in almost every thesis, but although the reaction is nice, I want to use another alternative, and up to this point I only found this adamantane example.

Title: Re: Catalytic reactions that improved existing reactions
Post by: Enthalpy on August 21, 2019, 04:48:16 AM

This one too looks magic to me: obtain efficiently a cycle with double bonds from varied hydrocarbons in hot air
https://en.wikipedia.org/wiki/Maleic_anhydride
Wiki mentions a catalyst.

Title: Re: Catalytic reactions that improved existing reactions
Post by: hypervalent_iodine on August 21, 2019, 08:18:10 AM

Quote from: Oropimente on August 20, 2019, 12:37:38 PM

So, I found this example of Reppe's [2+2+2+2] cycloaddition reaction as an example of using catalytic systems that improved the synthesis of a otherwise difficult compound in a thesis.

(https://i.ibb.co/xLKX1Bp/IMG-1339.jpg)
Reppe and coworkers, Justus Liebigs Ann. Chem. 1948, 560, 1, for the Ni reaction.

Are there another examples of reactions like this one? Like the synthesis of adamantane (https://en.wikipedia.org/wiki/Adamantane) from dicyclopentadiene, which is awesome. I'm asking because in our group we use that Reppe example in almost every thesis, but although the reaction is nice, I want to use another alternative, and up to this point I only found this adamantane example.

This is kind of relevant, but you can make COT reasonably easy by throwing Rh catalysts at cubane. You can generate substituted COT this way also. The group I work in has a paper on this if you’re interested: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201805124 and https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201806277