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Does this reaction work in theory? It's based on the Simmons–Smith reaction but with ZnCCl$_4$ instead of ZnCH$_2$Cl$_2$.enter image description here

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    $\begingroup$ I doubt it. S-S is overwhelming done with di-iodo or dibromomethane. Dichloromethane is often used as solvent but does not participate. $\endgroup$
    – Waylander
    Sep 14 at 15:36
  • $\begingroup$ ZnCCl4 is not possible. At least, I don't know. Can you link me where did you find this compound? $\ce{ZnCH2Cl2}$ also does not exist as a sole compound as it is a carbenoid intermediate made from the reaction of DCM and zinc. $$\ce{2CH2Cl2 + 2Zn -> [2ClCH2ZnCl] <=> (ClCH2)2Zn + ZnCl2}$$ $\endgroup$ Sep 15 at 2:52
  • $\begingroup$ @NilayGhosh I didn't see it anywhere. My thought was that if $\ce{ZnCH2Cl2}$ makes a compound with 2 hydrogens, $\ce{ZnCCl4}$ would make a compound with 2 chloride atoms attached. $\endgroup$
    – bobsburger
    Sep 17 at 14:22
  • $\begingroup$ But that compound isn't possible. $\endgroup$ Sep 18 at 1:51

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