I want to conduct nucleophilic addition/substitution reaction on ferrocene carboxaldehyde. May I know the feasibility?
Hi there,
As far as I know, since there is no leaving group on aldehydes, they only undergo nucleophilic additions.
Hope it helps.
It really depends on what you want to acomplish. In theory, under basic conditions, you should be able to react it with an acid derivative (thioester, anhydride, acyl halide). From that, one could assume, in theory, that this mechanism would allow for example the addition of other anions like sulfonates, borates, phosphates, etc. I don't know much about metallocene chemistry, but to me at least it would make more sense to carry the reaction on the ciclopentadienyl anion since the iron may interact with a variety of reactants, but again, it totally depends on what reaction you want to acomplish. Nucleophilic addition however should be able to be done rather easily.
nucleophilic addition between carbonyl compound (aldehydes and ketones) and Hydrogen cyanide, HCN, to produce hydroxynitriles (for example: 2-hydroxypropanenitrile, 2-hydroxy-2-methylpropanenitrile)
Dear all,
Thank you very much for your valuable answers and time.
I have created carbanion in my system/reaction mixture then I want to add ferrocene carboxaldehyde. It has an aldehyde group on ferrocene.
Nucleophilic addition reactions are an important class of reactions that allow the interconversion of C=O into a range of important functional groups.
Aldehydes undergo nucleophilic addition reactions, not substitution. Even a Wittig reaction is an addition of the ylid to the carbonyl, followed by loose of thiphenylphosfine oxide.
Nucleophilic addition is a typical reaction of carbonilic compounds. Aldehydes are more reactive than ketones, owing to the presence of a more electrophilic sp2 carbon atom. Elimination of H2O may follow, giving a new unsatured species, but sometimes the tetrahedral adduct is stable enough to be isolated.
Dear Billa
Aldehydes undergo nucleophilic addition reactions with elimination of H2O
Not always: elimination of water occurs e.g. in the aldol condensation, but not e.g. in addition of a Grignard reagent.
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