AI Article Synopsis
- The study found that the formation of doubly interlocked [3]rotaxanes affects the yield of simpler [2]rotaxanes when using bipyridine in the AT-CuAAC reaction.
- By adjusting reaction conditions, researchers achieved nearly full yields of [2]rotaxanes and successfully produced challenging [3]rotaxanes in up to 50% yield through a single reaction.
- The impact of the macrocycle's structure on these outcomes led to the proposal of a new mechanism for forming [3]rotaxanes.
Article Abstract
We recently identified competitive formation of doubly interlocked [3]rotaxanes as the origin of the non-linear variation in yield of [2]rotaxane with macrocycle size in the bipyridine-mediated AT-CuAAC reaction. Selection of reaction conditions gave [2]rotaxanes in essentially quantitative yield in all cases and hard to access doubly threaded [3]rotaxanes in up to 50% yield in a single, four component coupling. Based on the effect of macrocycle structure on the reaction outcome we propose a detailed mechanism of [3]rotaxane formation.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5645920 | PMC |
| http://dx.doi.org/10.1039/c4sc03999h | DOI Listing |
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