Thermal Claisen rearrangement of N-allylanilines

Journal Article · Wed Aug 20 00:00:00 EDT 1986 · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF00952923· OSTI ID:6416867

Abdrakhmanov, I B; Saraeva, Z N; Nigmatullin, N G; Tolstikov, G A

Thermal Claisen rearrangement of N-allylanilines in undecane is accompanied by a parallel reaction involving elimination of the allyl fragment. The former reaction proceeds according to a (3,3)-sigmatropic mechanism with a varied structure of transition state, depending on the nature of the allyl substituent. The rearrangement of N-(2-chloro-1-methyl-2-butenyl)aniline has an autocatalytic nature on account of the HCl formed on elimination of the allyl fragment. The initial formation of an unreactive complex with composition (amine):(HCl) = 2:1, which decomposes by the action of a second HCl molecule, is postulated.

• Research Organization: Institute of Chemistry, Ufa, USSR
• OSTI ID: 6416867
• Journal Information: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 35:2; ISSN BACCA
• Country of Publication: United States
• Language: Russian

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
AMINES
ANILINE
AROMATICS
CATALYTIC EFFECTS
CHEMICAL BONDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CLAISEN CONDENSATION
CONFORMATIONAL CHANGES
ELECTRON SPIN RESONANCE
ENERGY
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
INFRARED SPECTRA
INORGANIC ACIDS
KINETICS
MAGNETIC RESONANCE
MASS SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
QUANTITY RATIO
REACTION KINETICS
RESONANCE
SPECTRA
TEMPERATURE DEPENDENCE