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Many electrophiles are chiral and optically stable. Typically chiral electrophiles are also optically pure. One such reagent is the fructose-derived organocatalyst used in the Shi epoxidation. [11] The catalyst can accomplish highly enantioselective epoxidations of trans-disubstituted and trisubstituted alkenes.
Carboximidates are good electrophiles and undergo a range of addition reactions; with aliphatic imidates generally reacting faster than aromatic imidates. [2] They can be hydrolyzed to give esters and by an analogous process react with amines (including ammonia) to form amidines.
The general structure of a silyl enol ether. In organosilicon chemistry, silyl enol ethers are a class of organic compounds that share the common functional group R 3 Si−O−CR=CR 2, composed of an enolate (R 3 C−O−R) bonded to a silane (SiR 4) through its oxygen end and an ethene group (R 2 C=CR 2) as its carbon end.
A nitrogen bound to both a good electrofuge and a good nucleofuge is known as a nitrenoid (for its resemblance to a nitrene). [2] Nitrenes lack a full octet of electrons are thus highly electrophilic; nitrenoids exhibit analogous behavior and are often good substrates for electrophilic amination reactions.
Other electrophiles are aromatic diazonium salts in diazonium couplings, carbon dioxide in the Kolbe–Schmitt reaction and activated carbonyl groups in the Pechmann condensation, hydroxycarbenium ion in the Blanc chloromethylation via an intermediate (hydroxymethyl)arene (benzyl alcohol), chloryl cation (ClO 3 +) for electrophilic perchlorylation.
The negative oxygen was 'forced' to give electron density to the carbons (because it has a negative charge, it has an extra +I effect). Even when cold and with neutral (and relatively weak) electrophiles, the reaction still occurs rapidly. The phenolate has a negatively charged oxygen.
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Only the strongest electrophiles are able to do this, and these are usually dications or, more rarely, monocations, [10] [11] since high electrophilicity is accompanied by a substantial lack of electrons. In contrast, it is impossible for nucleophiles, which provide electrons for bond formation, to bind a noble gas strongly, because noble gases ...