Abstract
Publisher Summary This chapter discusses the occurrence, formation, properties, and structure of cyclopropane compounds. Preparative methods, general chemical and physical properties, and structure of these compounds are examined with illustrative examples. The detection of cyclopropyl groups in organic compounds is also analyzed. The behavior of unsaturated hydrocarbons, such as cyclopropenes, vinylcyclopropanes, arylcyclopropanes, the cyclopropenylium cation, and related compounds is compared with the saturated hydrocarbons. Functional derivatives of cyclopropane include halogen derivatives, organometallic compounds, and alcohols such as cyclopropanols, cyclopropylcarbinols and their derivatives, nitrocyclopropanes, sulfur derivatives, amines, such as cyclopropylamines, cyclopropylalkylamines, diazo compounds, aldehydes, and ketones. Cyclopropane- and cyclopropene-carboxylic acids, cyclopropyl carbanion, and cyclopropyl radicals are also discussed. Examples of aldehydes and ketones derived from cyclopropanes are cyclopropanecarbaldehyde and cyclopropanone, respectively. In hydrogen-donating solvents or in the presence of radical traps, cyclopropyl radicals derived from the optically active acid give racemic products containing the cyclopropyl ring. The flower heads of pyrethrum, Chrysanthemum cinerariifolium , contain four highly insecticidal components, which are esters giving on complete hydrolysis one of the two cyclopropanecarboxylic acids—namely, chrysanthemummono- and chrysanthemumdi-carboxylic acids. These are examples of natural products containing a cyclopropyl ring.
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