For the reaction of diethyl malonate with $\ce{NH2NH2}$ in aqueous medium in presence of $\ce{CH3CH2OH}$, I found two types of product with SciFinder:


In presence of $\ce{H2SO4}$, the reaction changes to:


$\ce{EtOH}$ is a good leaving group, but can you explain why there are two different types of products? With what mechanism can they be explained?

  • $\begingroup$ The second reaction looks similar to the Nazarov cyclization. The sulfuric acid must dehydrate and provide the protic properties required for the ring formation. $\endgroup$
    – Technetium
    Nov 26 '15 at 3:26
  • $\begingroup$ Can you please explain in detail about Nazarov cyclization? $\endgroup$ Nov 26 '15 at 3:27
  • $\begingroup$ I can't provide a proper answer in the acceptable format for this site on my cheap phone sorry but type it in to Google there's plenty of credible information about it (: $\endgroup$
    – Technetium
    Nov 26 '15 at 3:31
  • $\begingroup$ Try @ Nazarov cyclization reaction Wikipedia. $\endgroup$
    – Technetium
    Nov 26 '15 at 3:34

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.