Accession Number : AD0768799

Title :   Reactions of Activated Olefinic and Aromatic Systems with Cyanide Ion and with Certain Carbanions in Aprotic Solvents.

Descriptive Note : Final rept. 28 Apr 65-30 Jun 73,

Corporate Author : ILLINOIS UNIV URBANA

Personal Author(s) : Snyder,Harold R.

Report Date : 26 SEP 1973

Pagination or Media Count : 5

Abstract : The report briefly reviews results and publications from a research study on anion attack on conjugated systems. In dipolar aprotic solvents (DMSO, DMF) heavily arylated olefinic compounds having one or more double bonds activated by conjugation with the aromatic systems undergo reversible addition of cyanide ion to give carbanions which can be transformed into other substances, including the products of cyanation and hydrocyanation of the original hydrocarbons. Aromatic nitriles, particularly those containing polynuclear aromatic systems, also undergo addition of cyanide ion in a process which is useful in synthesis, including the synthesis of C-14 labelled nitriles. Aromatic ketones react with cyanide ion similarly but less readily, and aromatic nitro compounds are more reactive than nitriles and can be converted to a number of further transformation products. (Modified author abstract)

Descriptors :   (*CYANIDES, *ADDITION REACTIONS), (*NITRILES, CHEMICAL REACTIONS), (*AROMATIC COMPOUNDS, ADDITION REACTIONS), IONS, ALKENES, SYNTHESIS(CHEMISTRY), KETONES, ANTHRACENES

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE