Cyclopropene

-36 ° C

277.1 kJ / mol

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Cyclopropene is a cyclic organic compound having the empirical formula C3H4. It is the simplest cycloalkene and consists of a three -membered ( triangular ) ring containing one double bond. Cyclopropene is one of the most strained ring compounds which have been isolated so far. It is even more strained than cyclopropane because two bond angles of 120 ° to 60 ° - 60 ° so - must be reduced ( cyclopropane: 109.5 ° - 60 ° = 49.5 °). In nature, higher fatty acids are found that contain a cyclopropene ring, such as the Sterculinsäure in seed oil of Sterculia foetida.

Synthesis

Cyclopropylamine is methylated with methyl iodide exhaustive. The resulting iodide salt is reacted with moist silver hydroxide. The subsequent dry distillation of Cyclopropyltrimethylammoniumhydroxids supplies by Hofmann elimination cyclopropene:

Reactivity

Because of its high ring strain cyclopropene is very unstable and has a strong tendency to polymerize. Bromine is added to form 1,2- Dibromcyclopropan, the reaction proceeds very violently because of the ring strain.