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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 .
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.
In the carbylamine reaction (also known as the Hofmann isocyanide synthesis) alkali base reacts with chloroform to produce dichlorocarbene. The carbene then converts primary amines to isocyanides. Illustrative is the synthesis of tert -butyl isocyanide from tert -butylamine in the presence of catalytic amount of the phase transfer catalyst ...
The World of Chemistry is a television series on introductory chemistry hosted by Nobel Prize-winning chemist Roald Hoffmann.The series consists of 26 half-hour video programs, along with coordinated books, which explore various topics in chemistry through experiments conducted by Stevens Point emeritus professor Don Showalter the "series demonstrator" [1] and interviews with working chemists ...
The videos feature various experiments and demonstrations of the elements, some too dangerous to be performed in a classroom. [ 5 ] [ 8 ] Though the presenters take appropriate precautions when doing such experiments and provide adequate warnings, some scientists have criticized the dangerous experiments fearing people might try them at home ...
The Ugi reaction has been applied in combination with an intramolecular Diels-Alder reaction [16] in an extended multistep reaction. A reaction in its own right is the Ugi–Smiles reaction with the carboxylic acid component replaced by a phenol. In this reaction the Mumm rearrangement in the final step is replaced by the Smiles rearrangement. [17]
The Suárez modification of the Hofmann–Löffler–Freytag reaction was the basis of the new synthetic method developed by H. Togo et al. [42] [43] The authors demonstrated that various N-alkylsaccharins (N-alkyl-1,2-benzisothiazoline-3-one-1,1,-dioxides) 77 are easily prepared in moderate to good yields by the reaction of N-alkyl(o-methyl ...
If Hoffmann's model were correct, then the aldol addition would be the rate-limiting step, which accords with the absent kinetic isotope effect. [4] However, Hoffman's mechanism rationalizes neither the product's autocatalysis nor (in the reaction of aryl aldehydes with acrylates) the considerable generation of a dioxanone byproduct.