The cyclopropene pyrolysis story.
Cyclopropene is the last of the small strained ring hydrocarbons to have its thermal decomposition subjected to intensive investigation. This critical review describes the nearly 40 year history of this investigation largely by gas kinetic methods with chromatographic analysis. These studies have revealed that cyclopropenes can decompose by a variety of mechanisms involving diradicals, vinylcarbenes and vinylidenes. Much detailed information has been obtained about the reactivity of these intermediates which has wider implications for thermal hydrocarbon pyrolysis. Theory has also played a important role. Cyclopropene itself has been shown to be an intermediate in the allene --> propyne rearrangement. The story itself illustrates how the evolution of mechanistic understanding has been anything but straightforward.
Walsh
Robin
R
School of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, UK. r.walsh@reading.ac.uk
D003521:Cyclopropanes / Q000737:chemistry*; D005740:Gases / Q000737:chemistry; D006358:Hot Temperature; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics
D003521:Cyclopropanes; D005740:Gases; C021985:cyclopropene