ENDA

CAS 1572-59-4, Cat. No EN300-1723572
Carbene and carbenoid precursor

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Ethyl 2-diazo-2-nitroacetate (ENDA) is a nitro-diazo reagent used as a precursor to nitrocarbenes and acyl nitroso species¹. It engages in metal-catalyzed cyclopropanation (Rh, Co, Cu) of alkenes and alkynes, forming cyclopropanes and cyclopropenes, and can undergo ring-expansion to cyclic nitronates. ENDA also performs efficient O–H insertion (alcohols) and N–H insertion (anilines), including urea-catalyzed arylation cascades to give α-amino-α-aryl and α-diaryl esters. Upon heating or photolysis, it rearranges to acyl nitroso intermediates that participate in Diels–Alder, ene, and nucleophilic addition reactions. It is a stable, cold-stored diazo reagent.

Synonyms: ethyl nitrodiazoacetate; ethyl 2-diazo-2-nitroacetate; ENDA; 2-diazo-2-nitroacetic acid ethyl ester