Noel O'Boyle wrote:
> Uncle Al claims no possible SMILES for his chiralanes:
> 
> http://www.coronene.com/blog/?p=1128#comment-8794
> 
> Perhaps a worthy challenge for our new stereocode....

I'm not sure what the challenge is.  The molecule plainly has a distinct mirror 
image.  Ignoring hydrogens, there are four symmetry classes before you even 
take stereochemistry into account.  If we number the symmetry classes 1 
(starting in the center) through 4 (the farthest carbons from the center), then 
it's easy to see that for class 3, there are left- and right-handed 
connections.  That difference would propagate to class 2, and to class 1.

Why does Uncle Al say it "can't be stereolabeled even in principle"?  Am I 
overlooking something?

This is the same idea as a number of other situations we've seen, where the 
stereo labelings of one atom are only distinguished by the stereo labels of 
other atoms.  It's tricky, but not impossible.

(And who is "Uncle Al"? in real life?)

Craig


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