1-Cyanocyclopropanecarboxylic acid

Crum Brown-Walker reaction, 4 Cuprous chloride, 42, 121 1-Cyanocyclopropanecarboxylic acid, 69... 

TABLE 6. Parameters of 1 -cyanocyclopropanecarboxylic acid (68) from an XD study... 

When treated with a tetraalkylammonium fluoride, various 1-substituted trimethylsilylcyclo-propanes are converted to tetraalkylammonium salts of the corresponding cyclopropyl anions. Such anions are trapped by performing the reaction in the presence of an aldehyde, a ketone or carbon dioxide. The reaction is carried out successfully with electron-donating and electron-withdrawing substituents a to the silyl moiety. The best yield was obtained when methyl 1-trimethylsilylcyclopropanecarboxylate was treated with tetrabutylammonium fluoride in tetra-hydrofuran and acetaldehyde, methyl l-(l-hydroxyethyl)cyclopropanecarboxylate (la) was obtained in 90% yield.Under similar conditions (Z)-2,6-dimethyl-l-[(l-trimethylsilylcy-clopropyl)methylene]cyclohex-2-ene was transformed to (Z)-l- [l-(l-hydroxy-l-methyl-ethyl)cyclopropyl]methylene -2,6-dimethylcyclohex-2-ene (2) in 90% yield in the presence of acetone.Similarly, when carbon dioxide was used as electrophile in the presence of cesium fluoride, typically 1-trimethylsilylcyclopropane-l-carbonitrile was converted quantitatively to 1-cyanocyclopropanecarboxylic acid (3a). ... 

Cyanocyclopropanecarboxylic acid can be prepared by reaction of the dibromide with ethyl cyanoacetate (86% yield). ... 

Cyclopropane-1,1-dicarboxylic acid. This compound can be obtained in high yield by double alkylation of diethyl malonate with 1,2-dibromoethane under phase-transfer conditions. Malonic acid cannot be alkylated in this way. 1-Cyanocyclopropanecarboxylic acid can be prepared by reaction of the dibromide with ethyl cyanoacetate (86% yield), ... 

Cuitius rearrangement, 564 2-Cyanobenzyl cyanide, 541 Cyanoboration, 535-536 1-Cyanocyclopropanecarboxylic acid, 42 Cyanogen bromide, 148-149... 

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