Henry Rzepa's Blog Chemistry with a twist

October 30, 2010

Rate enhancement of the Diels-Alder reaction inside a cavity

Reactions in cavities can adopt quite different characteristics from those in solvents. Thus first example of the catalysis of the Diels-Alder reaction inside an organic scaffold was reported by Endo, Koike, Sawaki, Hayashida, Masuda, and Aoyama[1], where the reaction shown below is speeded up very greatly in the presence of a crystalline lattice of the anthracene derivative shown below.

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References

  1. K. Endo, T. Koike, T. Sawaki, O. Hayashida, H. Masuda, and Y. Aoyama, "Catalysis by Organic Solids. Stereoselective Dielsāˆ’Alder Reactions Promoted by Microporous Molecular Crystals Having an Extensive Hydrogen-Bonded Network", Journal of the American Chemical Society, vol. 119, pp. 4117-4122, 1997. http://dx.doi.org/10.1021/ja964198s

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