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Topic: reactivity explanation  (Read 1896 times)

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Offline medist

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reactivity explanation
« on: February 28, 2014, 01:36:50 PM »
Can some one help me in explaining the higher reactivity of 4-Phenyl-1,2,4-triazoline-3,5-dione in cyclo addtitions than any other dienophiles?

Offline TheUnassuming

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Re: reactivity explanation
« Reply #1 on: February 28, 2014, 02:16:24 PM »
In general what makes a dienophile better or worse (electronically) to engage in cycloadditions (could the substitution of nitrogens vs carbons or the benzyl vs esters make the necessary shift to the HOMO)? 
Do you think steric constraints of being in a ring could shift the Pi* orbitals to a more favorable position? 
When in doubt, avoid the Stille coupling.

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