Simmons-Smith Rxn

[Extirpator]

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Not sure how many have used the book organic odyssey, but in chapter #6 he claims that this rxn can be done using only an alkene and CHCl3 in (CH3)3CO3O-Na+... to form the normal product of a simmos-smith, in this case a (trans)-1,1-dichloro-2,3-diethylcyclopropane...

I thought you needed something with iodine and zinc? Everywhere I have looked on the web confirms this.. am I missing something?

Edit: I drew this real quick on marv sketch to avoid any confusion

 

[loveoforganic]

That's a cyclopropane formation reaction, but it's most definitely not a simmons-smith. What's happening in that reaction is you deprotonate the trichloromethane with the base, chloride spontaneously leaves, and you end up with a methyl carbene with two chlorine substituents. Carbenes are electron deficient species, and thus it adds to the alkene.

The simmons-smith product's only substituents are those that were originally on the alkene.

 

[Extirpator]

Alright, thanks. That's kinda what I thought, but I figured I better make sure just in case I get asked to name a simmons-smith rxn ha. Thanks again🙂