[Rutherford]

Does this reaction scheme make any sense? Should the diazo-acetate cause cyclopropanation? The cyclobutane with a double bond seems very unstable. The LiAH₄ isn't reducing the imine group .

[kriggy]

I find very dificult to belive that LiAlH₄ doesnt reduce that imine bond, just because its usualy used in excess (as far as I know).

[Rutherford]

What about the other stuff I mentioned? I find this very unusual. Diazoacetate normally doesn't behave that way.

[kriggy]

I dont know, I´ve never seen something like this. I think the proton in diazoacetate will be very acidic so Im not sure if it would accept the proton like its in the 2nd step. But its just my guess.
What about this:
http://en.wikipedia.org/wiki/Cyclopropanation#Using_diazo_compounds
?
btw I realy like those type of qustions, it makes me search stuff.. Instead of doing something else

[Rutherford]

Yeah, it should cause cyclopropanation as I initially wrote.
If all the reagents and the starting compound remain the same I would propose the attached compound as the final product.