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Need help with mechanism

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Gameofketones:
The correct option is (a). Is this Shapiro reaction? If so, can anyone help me out with the mechanism..I know the base abstracts the proton with Nitrogen but how does the ring reduce?

AWK:
? May be this one.

Enthalpy:
For my personal information:
how reasonable is a prediction for such unstable compounds?

AWK:

--- Quote from: Enthalpy on August 03, 2020, 04:59:50 AM ---For my personal information:
how reasonable is a prediction for such unstable compounds?

--- End quote ---
There are many more unstable compounds that chemists work with. The derivative of the compound drawn by me (ring substituted propionate ester) is the pheromone of American cockroaches.

hollytara:
I think this is Bamford-Stevens not Shapiro. 

Shapiro uses 2 equivalents of BuLi while Bamford-Stevens uses "base" in general, so can be done in protic or aprotic solvents.  Both go through a Diazo intermediate, depending on conditions this may make a carbene (aprotic) or a carbocation (protic). 

So imagine a carbene or carbocation was formed where the N attaches to the ring.  How would that lead to what you find?

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