5
$\begingroup$

enter image description here

What is the mechanism of this reaction? After performing $\ce{E1}$ thrice I was expecting 1,2,3-trimethylidenecyclopropane to be formed instead.

enter image description here

I know it's highly strained but I couldn't adopt any other pathway to reach any other product.

Is the triene product not formed at all? If cyclopropane-1,2,3-trione can exist I think even the triene product can.

This reaction is from my exercise book, couldn't find it on orgsyn.org.

$\endgroup$
  • 2
    $\begingroup$ This reaction does not show up in Scifinder. The triol is known though: Org Lett, 2007, 9, 2617 DOI:10.1021/ol070707r $\endgroup$ – Dennis Cao Jul 10 '18 at 17:01
  • 2
    $\begingroup$ No hits on Reaxys either. I strongly doubt it is real. $\endgroup$ – orthocresol Aug 1 '18 at 6:21
10
$\begingroup$

I have not written the steps for carbocation formation, simple dehydration.enter image description here

$\endgroup$
  • 6
    $\begingroup$ The mechanism is plausible, but I think it is still important to emphasise that this reaction is not known. There are zero reports of anybody getting benzene by treating the starting material with acid. Probably somebody made it up. $\endgroup$ – orthocresol Aug 1 '18 at 6:21
  • 8
    $\begingroup$ @ortho With a little foresight into this whole JEE business, you'll know that it's almost definitely made up ;-) $\endgroup$ – paracetamol Aug 1 '18 at 7:20
  • 5
    $\begingroup$ It looks nice on the paper. $\endgroup$ – mykhal Aug 1 '18 at 12:07

Your Answer

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

Not the answer you're looking for? Browse other questions tagged or ask your own question.