The reaction between furans and maleimides has increasingly become a method of interest as its reversibility makes it a useful tool for applications ranging from self-healing materials, to self-immolative polymers, to hydrogels for cell culture and for the preparation of bone repair. However, most of these applications have relied on simple monosubstituted furans and simple maleimides and have not extensively evaluated the potential thermal variability inherent in the process that is achievable through simple substrate modification. A small library of cycloadducts suitable for the above applications was prepared, and the temperature dependence of the retro-Diels-Alder processes was determined through in situ H NMR analyses complemented by computational calculations. The practical range of the reported systems ranges from 40 to>110 °C. The cycloreversion reactions are more complex than would be expected based on simple trends expected based on frontier molecular orbital analyses of the materials.
AbstractCarbohydrates, in the form of chitin, chitosan and cellulose, are one of the most available, renewable, and sustainable chemical feedstocks. Their conversion to biofuels, fine chemicals, and industrially-relevant monomers is becoming increasingly viable and promising as innovation decreases the price of this technology, and climate change and the price of fossil fuels increases the social and economic costs of using traditional feedstocks. In recent years, carbohydrates have been increasingly used as sources for nitrogen-containing fine chemicals. This chapter, with 86 references, provides a brief overview of the conversion of carbohydrate biomass to the standard hydrocarbon and oxygen-containing derivatives, and then provides a survey of recent progress in converting the biopolymers, and the derived mono and di-saccharides, into nitrogen-containing molecules with a special focus on N-heterocycle synthesis for medicinal applications.
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