Methylenecyclopropane is an organic compound with the formula . It is a hydrocarbon which, as the name suggests, is derived from the addition of a methylene () substituent to a cyclopropane ring. It is a colourless, easily condensed gas that is used as a reagent in organic synthesis.
Synthesis Methylenecyclopropane can be synthesized via an intramolecular cyclisation reaction from methallyl chloride by treatment with a strong base such sodium amide—sodium tert-butoxide (yield 43%) or sodium bis(trimethylsilyl)amide with further treatment by sodium tert-butoxide (yield 72%). Sodium tert-butoxide is used to isomerize byproduct 1-methylcyclopropene into methylenecyclopropane.
Reactions Being a strained and unsaturated molecule methylenecyclopropane undergoes many reactions, especially in the presence of metal catalysts. For example, methylenecyclopropanes can be converted to cyclobutenes in the presence of a platinum catalyst.PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes Alois Fürstner and Christophe Aïssa J. Am. Chem. Soc.; 2006; 128(19) pp 6306 -6307; Abstract This can be considered similar to the ring expansion seen in vinylcyclopropane rearrangements
Substituted methylenecyclopropanes can also be involved in trimethylenemethane cycloaddition reactions.
See also Methylenecyclopropene 1-Methylcyclopropene Methylcyclopropane Cyclopropene
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