Abstract
Abstract Reaction of α-carboxy-β-carbethoxy-γ,γ-dimethylbutyrolactone (3) with equimolar amount of nitrous acid gave ethyl α-hydroxyaminoaconate (7). However, the nitrosation of 3 using excess nitrous acid afforded a variety of compounds such as α-diazo (4 and 5), α-nitro (8), and α-azoxybutyrolactone (9) derivatives. Each of the products (4, 5, 8, and 9) could be synthesized from 7, independently. By the action of phosphoric acid, α-diazolactones (4 and 5) were converted into ethyl α,β-epoxyparaconate (6). The nature of the product 7 was demonstrated through its conversion into ethyl α-hydroxyaconate and through its thermal decomposition to ethyl α-aminoaconate and a-isopropylidenecyanoacetic acid derivatives. A possible mechanism for the formation of 6 through 4 and 5 is described.
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