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A complexed electrophile can contribute to the stability of arenium ions.

The mechanism of the Mannich reaction starts with the formation of an iminium ion from the
amine and the formaldehyde.

The compound with the carbonyl functional group (in this case a ketone) can tautomerize to the
enol form, after which it can attack the iminium ion.
Oxonium ion fates: In a mechanism step where one of the reactants is an oxonium
ion, that oxonium ion generally reacts in only one of four ways.

Oxonium ion fate #1: Ionization to form a carbocation. Water and alcohols are
moderate leaving groups. Ease of this ionization depends strongly on the stability
of the carbocation product.

Oxonium ion fate #2: Deprotonation. An oxonium ion O-H bond is

strongly acidic (R2OH+ pKa ~ -2).

Oxonium ion fate #3: Elimination to form a pi bond. Water and alcohols are
moderate leaving groups.

Oxonium ion fate #4a: Nucleophilic attack (at sp3 carbon). When the oxonium
ion has an sp3 carbon with low steric hindrance, it can undergo an SN2 nucleophilic

Oxonium ion fate #4b: Nucleophilic attack (at a carbonyl carbon). When
the oxonium ion is a protonated carbonyl group, the carbonyl can accept
a nucleophile at the carbon atom, producing a tetrahedral adduct. This is one of the
three common carbonyl fates.
It is similar to the mechanism that was proposed by Dewar and Landman for the formation of Tr and
H from the Tol [11]. This mechanism begins with a hydrogen migration in the Tol , from the methyl
group to the ipso position of the six-membered ring to form the first intermediate (Int1). Formation
of a bond between the methyl carbon and an alpha carbon produces the second intermediate (Int2).
This intermediate is composed of a six-membered ring and a threemembered ring (norcaradienyl
ion). Dissociation of the bond common to the rings in a disrotatory fashion produces a
cycloheptatriene intermediate (Int3). The last step in the formation of the tropylium ion and atomic
hydrogen is a hydrogen cleavage from the former methyl carbon in the cycloheptatriene