Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: FRK on August 10, 2016, 02:56:48 PM
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Does anybody know off the top of their head of any compounds that are liquid at room temperature that undergo retro-Diels-Alder at <250 C? Dicyclopentadiene is one that's commercially available that I know of.
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I was searching the department for things of this nature a few weeks ago, and it seems to be the go to if you can find it. I'd check the inorganic labs for things like cyclooctadiene (COD), or cyclooctatetraene (COT) which are common starting materials. Also things like azamethine ylides...
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Does anybody know off the top of their head of any compounds that are liquid at room temperature that undergo retro-Diels-Alder at <250 C? Dicyclopentadiene is one that's commercially available that I know of.
I remember as a postdoc having to trap a benzyne with furan (aromatic). The compound formed could be picked up in MS however I was unable to ever isolate it. If this is just for the sake of knowledge, draw the product you get via Diels-Aler of benzyne with furan, name it (ChemDraw helps these days), and search to see its decomposition point.
Just a thought. Driving force for retroDA is restoration of aromaticity.
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1,4-Dihydro-1,4-epoxynaphthalene mp 54-56 C