Catalytic rearrangement of tris-(2-substituted-2-propenyl) cyanurates
This paper is concerned with the synthesis and rearrangement of tris-(2-methyl-2-propenyl) (I), tris-(2-fluoro-2-propenyl) (II), and tris-(2-chloro-2-propenyl) (III) cyanurates. The rearrangement was conducted in toluene solution in presence of CuCl/sub 2/ x 2H/sub 2/O at 118-120/sup 0/. The observed decrease of the rearrangement rate in the case of cyanurates (II) and (III) can probably be attributed deactivation of the double bond due to the strong negative inductive effect of the halogen atom and consequent hindering of complexation of the copper ion with the unsaturated ligand. The deviation of the reactivity of cyanurate (I), containing a CH/sub 3/ group exhibiting the +I effect as a substituent, from the sequence can by attributed to steric hindrance caused by the methyl group, preventing coordination with the bulky copper atom.
- OSTI ID:
- 6974613
- Journal Information:
- J. Appl. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Appl. Chem. USSR (Engl. Transl.); (United States) Vol. 60:3; ISSN JAPUA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
AZINES
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINE COMPOUNDS
COMPLEXES
CONFORMATIONAL CHANGES
COPPER CHLORIDES
COPPER COMPLEXES
COPPER COMPOUNDS
COPPER HALIDES
CYANURATES
DEACTIVATION
ENERGY
ESTERS
FLUORINATED ALIPHATIC HYDROCARBONS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
ISOMERIZATION
KINETICS
MATERIALS TESTING
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
STEREOCHEMISTRY
TESTING
TRANSITION ELEMENT COMPLEXES
TRANSITION ELEMENT COMPOUNDS
TRIAZINES