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In the absence of an electron-withdrawing group, the final product is the α-hydroxyphosphonate 3a and 3b.
When the multiple bond is polarized by an electron-withdrawing group, selective addition results.
Some interesting results were that electron-withdrawing groups on the diene decreased the rate of reaction.
E" is used in organic chemistry to denote an electron-withdrawing group. "
If next to an electron-withdrawing group, conjugate addition (Michael addition) occurs.
Hammett originally used a series of anilines with electron-withdrawing groups for the bases.
The opposite effect is seen when an electron-withdrawing group (such as nitro) is attached.
Strategically placed electron-withdrawing groups in the starting material can render this process essentially irreversible.
They are strong electron-withdrawing groups that increase the acidity of alpha-protons on the aromatic ring.
An additional stabilization is achieved by the trifluoromethyl group as a strong electron-withdrawing group.
The carboxyl is the better electron-withdrawing group, causing the β-carbon to be most electrophilic.
Suitable choice of electron-withdrawing groups allows selective 4-substitution of the pyrrole ring.
The substituent R next the amine methylene bridge is an electron-withdrawing group.
Alkenes with electron-withdrawing groups commonly bind strongly to low-valent metals.
Fluorine is a good electron-withdrawing group in terms of synthetic accessibility and biological inertness.
Therefore, these electron-withdrawing groups are meta directing.
Electron-withdrawing groups, such as groups with fluorine substitution, are necessary to stabilize these compounds.
Deprotonation of 1 by base leads to carbanion 2 stabilized by its electron-withdrawing groups.
Most sulfilimines are N-substituted with electron-withdrawing groups.
They lead to the models of resonance structures for an electron-withdrawing group and electron-releasing group on benzene.
Stabilizing the initially formed radical with electron-withdrawing groups provides access to more stable 6-endo cyclization products preferentially.
In other words, the electron-withdrawing groups resulted in "less unfavorable" electrostatic interactions in the ground state.
Electron donating groups on the imine facilitate this step, while electron-withdrawing groups impede the attack.
Electron-withdrawing groups in the N3 and C5 positions stabilize the carbenes more than electron-donating groups.