[newmiasis]

Ok, I'm wondering if this reaction is possible (it seems like it should be but I have not been able to find any examples, or any examples of the product actually existing)


I attached a sketch of this potential reaction. Does this reaction actually occur via SN2? I only drew the organic products, and I haven't shown stereochemistry - but I'd really love a simple answer from someone with experience.

It seems that this should occur, but I am unsure.

I'd really appreciate any help possible. Also, I don't believe there are any other possible products, but if I have written this reaction wrong, please let me know.


Thanks in advance

[movies]

It's not a S_N2 reaction because there isn't inversion of the stereochemistry.  It's more like an S_N1 reaction with retention of stereochemistry.  The rationale for the retention of stereochem is a non-classical carbocation intermediate.

[Arsenic]

Anchimeric assitance of the double bond  is likely to influence this reaction solely if the product you have shown is formed exclusively.

please view the following URL for more info:
http://www.cem.msu.edu/~reusch/VirtualText/rearrang.htm

what I think: In this reaction anchimeric assistance is not possible or is lessened due to the existance of an electron withdrawing group being attached to the double bond , hence the reaction should produce more than one product .

[Mitch]

Arsenic: Great post. 3 Karma points awarded.

[newmiasis]

Thanks Arsenic!

[movies]

Arsenic: Great post. 3 Karma points awarded.

I agree.  Nice job.