Mechanism Page

Check out our Mechanism:

 

Maybe You want to see it when its not moving.......

Our Mechanism doesn't Move 1) In the first step, we see the triphenylphosphine get a little jealous of the Cl on the NCS. It acts as a good acid as it pulls the Cl off. This allows for a resonating effect which moves the double bond through the NCS leaving the Oxygen with a negative charge producing:
2-oxo-3,4-dihydro-2H-pyrrol-5-olate.
2) In step two, we see the 2-oxo-3,4-dihydro-2H-pyrrol-5-olate reciprocate the envy towards Compound 59, as it deprotonates the OH. This forms pyrrolidine-2,5-dione which is a fairly stable compound. Meanwhile, the now deprotonated compound 59 decides that it wants the ClPPh3 and therefore bonds to the Phosphate from the ClPPh3. Unfortunately for Cl, it is a good leaving group, so it comes off the ClPPh3 and is left all alone.
3)
In a jealous rage, the Cl decides that it doesn’t want to be alone and comes in from the bottom of the compound, bumping off the OPPh3 simultaneously via SN2 reaction. This produces compound 46 with byproducts of pyrrolidine-2,5-dione and triphenylphosphine oxide.

 

 

Time to Go home

Click On The Bartender To Go Home

Home | Leading Question | Experimental | HNMR | Citation | About Us

Anna Shatsman, Eugene Lo, Mike VanHall