Nucleophilic attacks on carbon–carbon double bonds. Part XVIII. Reaction of 2-dicyanomethyleneindane-1,3-dione with anilines in acetonitrile

doi:10.1039/P29730001045

Paper

Nucleophilic attacks on carbon–carbon double bonds. Part XVIII. Reaction of 2-dicyanomethyleneindane-1,3-dione with anilines in acetonitrile

Published 1973 · Z. Rappoport, D. Ladkani

Journal of The Chemical Society-perkin Transactions 1

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Abstract

The replacement of one of the cyano-groups of 2-dicyanomethyleneindane-1,3-dione (II) by ring-substituted anilines in acetonitrile is of nearly second order in the amine, is catalysed by pyridines, and shows a Hammett ρ value of –6·9 at 30°. A mechanism is suggested in which the zwitterion (III), formed initially by a reversible nucleophilic attack of the amine on (II), is reversibly deprotonated by a second amine molecule, followed by an anilinium ion-assisted expulsion of the cyanide ion. NN-Dimethyl-, N-methyl-, 2,5-dimethoxy-, 2,6-dimethoxy-anilines give para-addition products with (II).

Study Snapshot

The reaction of 2-dicyanomethyleneindane-1,3-dione with anilines in acetonitrile is a nearly second-order nucleophilic attack, catalyzed by pyridines, with a mechanism suggesting reversible nucleophilic attack of the

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Nucleophilic attacks on carbon–carbon double bonds. Part XVIII. Reaction of 2-dicyanomethyleneindane-1,3-dione with anilines in acetonitrile

References

Citations

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