Is the Friedel-Crafts alkylation of benzene with cyclopropenyl chloride according to the following scheme feasible?

Friedel-Crafts alkylation of benzene with cyclopropenyl chloride

Would the attack of the benzene towards the cycopropylium take place? I am wondering about this, as the cyclopropyl carbocation is aromatic, which implies that it is highly stable. If it reacts with the benzene ring, it would lose the aromatic stabilisation, thus rendering it comparatively less stable.

  • $\begingroup$ If I were you I would go for PhLi + 3-chlorocyclopropene that seems to me to be more promising (and also far more convenient). $\endgroup$ – logical x 2 Nov 1 '16 at 21:52
  • $\begingroup$ Brief Reaxys search shows some related Lewis-acid catalysed arylations, but they start with 3,3-dichlorocycloprop-1-ene and end up with 3-arylcyclopropenyl cations $\endgroup$ – orthocresol Jan 25 '19 at 13:47
  • $\begingroup$ @orthocresol That's pretty interesting. What happens to the other chloride? $\endgroup$ – Zhe Jan 25 '19 at 13:57
  • $\begingroup$ @Zhe one chloride gets replaced with the aryl group, the other chloride is ionised $\endgroup$ – orthocresol Jan 25 '19 at 14:04
  • $\begingroup$ @orthocresol Sorry, I should've been clearer with my question: where does the hydride (or proton) come from that replaces that chloride? $\endgroup$ – Zhe Jan 25 '19 at 14:39

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