The nitroolefinic behavior of 4-nitrobenzodifuroxan

4-Nitrobenzodifuroxan (NBDF) is shown to possess a nitro-activated double bond of 1.339 Å, which exhibits a high reactivity both in normal and inverse electron demand Diels–Alder condensations. NBDF is also shown to react as a Michael acceptor. Altogether, the results reveal that the nitroolefinic character of NBDF is considerably higher than that of 4,6-dinitrobenzofuroxan.