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Results tagged with pericyclic
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user 4231
For questions concerning all aspects of pericyclic reactions, their use in synthesis, and the orbital analyses used to describe them.
21
votes
Accepted
Why is the exo product formed in the Diels–Alder reaction between furan and maleic anhydride?
Great question! It turns out that the rate of formation of the "expected" endo product is actually ~500 times faster than the rate of formation of the exo product. However, the Diels–Alder is a rever …
- 71.9k
10
votes
Accepted
Orbital correlation diagram for the cleavage of cyclopropylmethylene carbene
What is the type of the ring opening; is it a concerted or radical
based C-C bond cleavage?
This is a chelotropic reaction, a subset of cycloaddition\fragmentation reactions. As to whether it …
- 85.4k
3
votes
Relative rates of two acyclic dienes in the Diels-Alder reaction
You are correct that the having the diene in an s-cis conformation is extremely important. Only from this conformation can the Diels-Alder occur. If there is a high concentration of the s-cis conform …
- 85.4k
14
votes
Accepted
Singlet/triplet oxygen cycloadditions
Normal dioxygen ($\ce{O2}$) exists as a ground state, triplet biradical. This is an example of a molecule that, thermodynamically should be quite reactive, yet is kinetically unreactive - once again, …
- 85.4k
3
votes
Accepted
Torquoselectivity: Disrotatory ring opening
No, there is no general orbital symmetry rule for predicting which of the two possible disrotatory motions will be favored. However, by examining steric effects in the two possible transition states …
- 85.4k