Is there a table somewhere for what adds 1,2 vs. 1,4 to a,b-unsat. carbonyls?

This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.

theWUbear

Full Member
10+ Year Member
Joined
Jun 7, 2009
Messages
1,873
Reaction score
61
Is there a table somewhere showing which (common at least) nucleophiles add 1,2 vs. 1,4 to an alpha,beta-unsaturated carbonyl?

Tried to google it. Failed
 
I'm pretty sure that has to do with the temperature conditions of the reaction and whether or not the thermodynamic (1,4) or kinetic product (1,2) is formed. I think some of that has to do with whether the solvent is in excess or if the compound is in excess. Check under the "Michael" reaction for more details. Hope that was what you were referring to.
 
For beta-unsaturated carbons, check out the Michael Reaction, like Legit suggested. That reaction adds a nucleophile 1,5. Hit the molecule with the nucleophile (plus LDA) and then some base. The Stork reaction is the same with enamines, except acid instead of base at the last step.

If you want to add 1,2 or 1,4, you need alpha-unsaturated carbons and direct addition/alkylation/acylation.
 
Top