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The generic structure of a nitrene group. In chemistry, a nitrene or imene (R−:Ṅ·) is the nitrogen analogue of a carbene.The nitrogen atom is uncharged and monovalent, [1] so it has only 6 electrons in its valence level—two covalent bonded and four non-bonded electrons.
In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. [1] Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular.
In the Kinugasa reaction, a nitrone and a copper acetylide react to ultimately form a β-lactam. [12] [13] In the first step of this reaction, a metal acetylide is formed by reaction of the terminal alkyne with the copper salt. The 1,3-dipolar cycloaddition of the nitrone with the metal acetylide affords a 5-membered ring that rearranges to ...
In the Bamberger rearrangement N-phenylhydroxylamines rearrange to 4-aminophenols. The nucleophile is water. The Smiles rearrangement is the intramolecular version of this reaction type. Nucleophilic aromatic substitution is not limited to arenes, however; the reaction takes place even more readily with heteroarenes.
Example cheletropic reactions: Case 1: the single atom is the carbonyl carbon (C=O) that ends up in carbon monoxide (C≡O). Case 2: the single atom is the nitrogen atom in the diazenyl group (N=N), which ends up as dinitrogen (N≡N). The above are known as cheletropic eliminations because a small, stable molecule is given off in the reaction. [1]
Both rearrangement reactions involve a carbon to nitrogen shift, usually after electrophilic activation of the leaving group on the nitrogen atom. [4] [12] [13] The main difference in the starting materials, however, is their saturation degree.
Atom Y may be sulfur, selenium, or nitrogen. If Y is nitrogen, the reaction is referred to as the Sommelet–Hauser rearrangement if a quaternary ammonium salt is involved or the aza-Wittig reaction if an alpha-metalated tertiary amine is involved; if Y is oxygen, then it is called a 2,3-Wittig rearrangement (not to be confused with the well ...
The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [ 1 ] [ 2 ] [ 3 ] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.