AI Article Synopsis
- 2-Halo-3-tosyl-oxanorbornadienes can react with two thiol molecules, starting with a nucleophilic substitution to create oxabicyclic thiovinyl sulfones.
- These sulfones then undergo a thio-Michael addition with a second thiol, forming oxanorbornenic thioketals.
- The thioketals can fragment through retro-Diels-Alder reactions, producing a furan derivative and a ketene-acetal, with the reaction rate affected by the structure of the oxanorbornadienic skeleton due to electronic and steric factors.
Article Abstract
2-Halo-3-tosyl-oxanorbornadienes are able to accept two thiol molecules through an initial nucleophilic substitution, giving isolable oxabicyclic thiovinyl sulfones that, subsequently, can react with a second thiol molecule via thio-Michael addition. The resulting oxanorbornenic thioketals undergo retro-Diels-Alder (rDA) fragmentation to release a furan derivative and a ketene ,-acetal. The substitution pattern of the oxanorbornadienic skeleton influences the rate of the rDA through electronic and steric factors examined by quantum mechanical calculations.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10594659 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.3c02548 | DOI Listing |
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