Cyclopropanecarboxylic acid amides

In the following we shall focus on heterogeneous acid-base reactions. One of the best known case studies is the reaction of crystalline benzoic acid with ammonia to form 1 1 ammonium salts [19, 20]. Crystalline p-chlorobenzoic anhydride reacts with gaseous ammonia to give the corresponding amide and ammonium salt [22] a similar reaction has been investigated in the case of optically active cyclopropanecarboxylic acid crystals [23]. 

Cyclopropylamines were also obtained from cyclopropanecarboxylic acids (73, R = OH), hydrazoic acid and sulfuric acid in a Schmidt reaction Cyclopropyl ketones (73, R = alkyl, aryl) as starting materials in the Schmidt reaction gave rise to a mixture of two isomeric amides (74 and 75) (equation 12). From ketones with an... 

The reagent reacts with an a,j8-unsaturated acid amide to give a pyrrolidone or a cyclopropanecarboxylic amide, or both, depending upon the substituents present. ... 

Various cyclopropanecarboxylic acids and esters have been converted to various amides, TV-alkylated amides, and hydrazides by treatment with ammonia, alkylamines, - and hydrazines, respectively. In many cases the acids have been converted via the corresponding acid chlorides generated in situ. Diethyl esters of a variety of cyclopropane-1,1-dicarboxylic acids also react with urea. Generally, all these reactions proceed smoothly and in fairly good yield and give only very small amounts of byproducts due to opening of the cyclopropane ring. 

Cyclopropyl ketones and lactams as well as amides of cyclopropanecarboxylic acids were converted to the corresponding thiocarbonyl compounds on reaction with 2,4-bis(4-methoxyphenyl)-l,3,2,4-dithiadiphosphetane-2,4-dithione (Lawesson s reagent) in benzene or toluene the yields were good. For example, reaction of lactam 1 to give thione 2. Thiones were also formed when hydrazones were treated with sulfur monochloride. ... 

Bromocyclobutanone shaken with at least 2 moles of satd. aq. Na-carbonate soln. until the startg. m. is dissolved cyclopropanecarboxylic acid. Y ca. 90%. Also amide and ethyl ester s. J.-M. Conia and J.-L. Ripoll, C. r. 251, 1071 (1960). 

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