[Tosyl1]

Hey,

What will happen if I add ethyl diazoacetate to HBr in ether solution? Obviously, diazoacetate would release N2 to form a carbene :CH-COOEt. But what happens next, not sure if it can react with ether?

[orgstudy]

 :delta:carbene don't react with ether as much as i know. it attacks unsaturated system

[AndersHoveland]

Thanks for bring this reaction to light. I had no idea about this potentially useful regent and its cycloaddition reaction.
Does this reaction require a catalyst (such as copper or platinum) to proceed? such catalysts were mentioned in some literature

Would the RCH2: radical react with cyclopropane to form a cyclobutane derivitive? Does anyone know, or have opinions about this?

One revealing reaction:
Ketene CH2=C=O reacts with diazomethane, at (minus) -70degC, to first form cyclopropanone, and then reacts further with more diazomethane to form cyclobutanone (which boils at 98-100degC). Kaarsemaker (1951)

So it would appear that ethyl diazoacetate, which is a derivitive of diazomethane, could react with cause cyclopropanone to undergo a ring expansion to the cyclobutanone, but the question is would this work with plain cyclopropane? Any opinions?

http://www.novasep.com/technologies/diazomethane.asp
in a somewhat related reaction, apparently diazomethane can be reacted with acetylene to produce pyrazole

[Tosyl1]

Hey,

What will happen if I add ethyl diazoacetate to HBr in ether solution? Obviously, diazoacetate would release N2 to form a carbene :CH-COOEt. But what happens next, not sure if it can react with ether?

It might add to C-H bond of Et and form butyrolactone.

[orgopete]

I would be inclined to use the same reaction as formation of an ester with diazomethane. That would predict a different product. Sometimes HCl is used to quench excess diazomethane in a reaction.