A new feature in the chemistry of nitrobenzofuroxans: ambident reactivity in Diels–Alder condensations

Abstract

The 4,6-dinitrobenzofuroxan (DNBF) structure is shown to act both as a dienophile and a heterodiene upon treatment with 1-trimethylsilyloxybuta-1,3-diene and vinyl ethyl ether, providing in two steps a highly functionalised stereoselective compound.