Nitrone

A nitrone is the N-oxide of an imine Imine

An imine is a functional group [i] or chemical compound [i] containing a carbon [i]-nitrogen [i] double bond [i] ...

and a functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ...

in organic chemistry Organic chemistry

Organic chemistry is a specific discipline within the subject of chemistry [i]. ...

. The general structure is R1R2C=NR3+O-. A nitrone is 1,3-dipole in 1,3-dipolar cycloadditions. It reacts with alkene Alkene

In organic chemistry [i], an alkene, olefin, or olefine is an unsaturated [i] chemical compound [i] ...

s to an isoxazolidine Oxazolidine

Oxazolidine is a five-membered ring compound consisting of three carbon [i]s, a nitrogen [i], a hydrogen [i] ...

: One example of this reaction type is the reaction of various Baylis-Hillman adducts Baylis-Hillman reaction

The Baylis-Hillman reaction is an organic reaction [i] of an aldehyde [i] and an α,β-unsaturated [i] ...

with C-Phenyl-N-methylnitrone forming an isoxazolidine Oxazolidine

Oxazolidine is a five-membered ring compound consisting of three carbon [i]s, a nitrogen [i], a hydrogen [i] ...

in which R1 is phenyl Phenyl group

In chemistry [i], the phenyl group or phenyl ring is the functional group [i] with the formula ...

, R2 is hydrogen Hydrogen

|- | Triple point [i] || 13.8033 K, 7.042 kPa ...

and R3 is a methyl group .

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Encyclopedia

A nitrone is the N-oxide of an imine Imine

An imine is a functional group [i] or chemical compound [i] containing a carbon [i]-nitrogen [i] double bond [i] ...

and a functional group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ...

in organic chemistry Organic chemistry

Organic chemistry is a specific discipline within the subject of chemistry [i]. ...

. The general structure is R₁R₂C=NR₃⁺O^-.

A nitrone is 1,3-dipole in 1,3-dipolar cycloadditions. It reacts with alkene Alkene

In organic chemistry [i], an alkene, olefin, or olefine is an unsaturated [i] chemical compound [i] ...

s to an isoxazolidine Oxazolidine

Oxazolidine is a five-membered ring compound consisting of three carbon [i]s, a nitrogen [i], a hydrogen [i] ...

:

One example of this reaction type is the reaction of various Baylis-Hillman adducts Baylis-Hillman reaction

The Baylis-Hillman reaction is an organic reaction [i] of an aldehyde [i] and an α,β-unsaturated [i] ...

with C-Phenyl-N-methylnitrone forming an isoxazolidine Oxazolidine

Oxazolidine is a five-membered ring compound consisting of three carbon [i]s, a nitrogen [i], a hydrogen [i] ...

in which R_{1_{is phenyl Phenyl group

In chemistry [i], the phenyl group or phenyl ring is the functional group [i] with the formula
...

, R_{2_{is hydrogen Hydrogen

|-
| Triple point [i] || 13.8033 K, 7.042 kPa
...

and R_{3_{is a methyl group .

Nitrones react with terminal alkyne Alkyne

Alkynes are hydrocarbon [i]s that have at least one triple bond [i] between two carbon [i] atoms. ...

s and a copper salt to beta-lactam Beta-lactam

A beta-lactam ring or penam is a lactam [i] with a heteroatomic [i] ring structure [i], consistin ...

. This reaction is also called the The Kinugasa reaction for example in this reaction: :

The first step in this reaction is a dipolar cycloaddition of the nitrone with the in situ generated copper acetylide Metal acetylide

A metal acetylide is an alkyne [i] that has had a proton removed from the terminal end by a metal [i] su ...

to a 5-membered ring structure which rearranges in the second step.
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