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Courtesy of this Angewandte Chemie paper, in which we learn that "anti-Bredt" olefins - those C=C bonds located at the bridge of a caged bicyclic ring system - don't have to be discarded as possible structures for new natural products. The authors recommend their computational model, which uses modern forcefields to estimate olefin strain (OS) and predict stability of these bridgehead double bonds.
Happy Friday, everyone!
See Arr Oh
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*I know this is a bit belated, but RIP P.v.R. Schleyer. You seemed like a really interesting guy.
Many thanks, See Arr Oh.
ReplyDeleteThe stability of bridgehead olefins follows the stability of the respective trans cycloalkenes. The ring in the picture has 9 carbons along the perimeter, which would make its stability in line with that of trans-cyclononene, a perfectly stable molecule. It's only when you get smaller than that that things start getting unstable.
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