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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.

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    $\begingroup$ 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, 2018 at 17:01
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    $\begingroup$ No hits on Reaxys either. I strongly doubt it is real. $\endgroup$
    – orthocresol ♦
    Aug 1, 2018 at 6:21

1 Answer 1

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

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    $\begingroup$ 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, 2018 at 6:21
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    $\begingroup$ @ortho With a little foresight into this whole JEE business, you'll know that it's almost definitely made up ;-) $\endgroup$
    – paracetamol
    Aug 1, 2018 at 7:20
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    $\begingroup$ It looks nice on the paper. $\endgroup$
    – mykhal
    Aug 1, 2018 at 12:07

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