N-Formamides are important intermediates in the synthesis of many pharmacologically active compounds and are used as protecting groups for amines or as catalysts in different reactions. The current Nformylation experiment is designed as a part of an introductory organic chemistry course for undergraduate students. The experiment includes formylation of substituted aromatic amines using formic acid under solventfree conditions. Students are introduced to laboratory safety precautions, reaction mechanism, and basic laboratory techniques such as a solvent-free reaction setup, reflux, filtration, melting point determination, yield calculation, and lab report write-up. Students synthesized four different formamides in 50−80% yield as a straightforward application of nucleophilic substitution reactions.
The 2(H)-pyran-2-one bearing electron-donating tert-butylcarbamate (BocNH-) group at the 5- position is a “chameleon” diene and undergoes efficient Diels–Alder cycloadditions with alkene dienophiles with both electron-rich and electron-deficient substituents. Cycloadditions afford the 5-substituted bicyclic lactone cycloadducts regardless of the electronic nature of the dienophile. However, cycloadditions with electronically matched electron-deficient dienophiles proceed faster than those with electronically mismatched electron-rich dienophiles.
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