Hass–Bender Oxidation on:
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The reaction process begins with the deprotonation of 2-nitropropane at the α carbon to form a 
Although originally developed for benzyl compounds, the reaction also works for allyl halides, giving the respective α,β- enones and enals.
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, ...
, the Hass–Bender oxidation (also called the Hass–Bender carbonyl synthesis) is an organic oxidation reaction
Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions carr ...
that converts benzyl
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group () group.
Nomenclature
In IUPAC nomenclature, the prefix benzyl refers to a substi ...
halides into benzaldehydes
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.
It is a colorless liquid with a characteristic almond-like odor ...
using the sodium salt of 2-nitropropane as the oxidant. This name reaction A name reaction is a chemical reaction named after its discoverers or developers. Among the tens of thousands of organic reactions that are known, hundreds of such reactions are well-known enough to be named after people. Well-known examples include ...
is named for Henry B. Hass and Myron L. Bender, who first reported it in 1949.
:
The reaction process begins with the deprotonation of 2-nitropropane at the α carbon to form a resonance
Resonance describes the phenomenon of increased amplitude that occurs when the frequency of an applied Periodic function, periodic force (or a Fourier analysis, Fourier component of it) is equal or close to a natural frequency of the system ...
-stabilized anion
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...
. This compound then initiates an SN2 reaction to displace the benzyl halide. Unlike in the nitroaldol reaction
The Henry reaction is a classic carbon–carbon bond formation reaction in organic chemistry. Discovered in 1895 by the Belgian chemist Louis Henry (1834–1913), it is the combination of a nitroalkane and an aldehyde or ketone in the presence ...
, where the deprotonated carbon of the nitroalkyl group is the nucleophilic
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...
atom, it is instead an oxygen of the nitro itself that attacks the benzylic carbon. The ''O''-benzyl structure then undergoes a pericyclic reaction
In organic chemistry, a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in a concerted fashion, and the bond orbitals involved in the reaction overla ...
to produce a benzaldehyde, with dimethyloxime
In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted ...
as a byproduct.
:
Although originally developed for benzyl compounds, the reaction also works for allyl halides, giving the respective α,β- enones and enals.
References
Name reactions Organic oxidation reactions {{organic-chem-stub