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An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group – N + ≡C −. It is the isomer of the related nitrile (–C≡N), hence the prefix is isocyano. [1] The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks ...
In organic chemistry, isocyanate is the functional group with the formula R−N=C=O. Organic compounds that contain an isocyanate group are referred to as isocyanates . An organic compound with two isocyanate groups is known as a diisocyanate.
The carbylamine reaction (also known as the Hoffmann isocyanide synthesis) is the synthesis of an isocyanide by the reaction of a primary amine, chloroform, and base. The conversion involves the intermediacy of dichlorocarbene .
An example taken from "Name Reactions: Heterocyclic Chemistry" by Jie Jack Li shows a case of stereospecificity in the Bucherer–Bergs reaction. While the end product of the Bucherer–Bergs reaction is a hydantoin, the hydantoin can undergo hydrolysis to form an amino acid. This is what is assumed in the example below.
In a similar fashion, the intermediate isocyanate can be trapped by tert-butyl alcohol, yielding the tert-butoxycarbonyl (Boc)-protected amine. The Hofmann Rearrangement also can be used to yield carbamates from α,β - unsaturated or α- hydroxy amides [ 2 ] [ 8 ] or nitriles from α,β- acetylenic amides [ 2 ] [ 9 ] in good yields (≈70%).
In organic chemistry, the Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane (R−NO 2) to an aldehyde (R−CH=O) or a ketone (R 2 C=O) and nitrous oxide (N 2 O). The reaction has been the subject of several literature reviews. [1] [2] [3] The Nef reaction: 1. Salt of a nitroalkane ...
Chlorosulfonyl isocyanate is the chemical compound ClSO 2 NCO, ... [2+2]-cycloaddition to give the sulfonamide. The SO 2 Cl group can be removed simply by hydrolysis, ...
Isocyanide dichlorides are organic compounds containing the RN=CCl 2 functional group. Classically they are obtained by chlorination of isocyanides . Phenylcarbylamine chloride is a well-characterized example.