Methylenecyclopropane Knowpia

Methylenecyclopropane
Names
	Preferred IUPAC name Methylidenecyclopropane
Identifiers
CAS Number	6142-73-0;
3D model (JSmol)	Interactive image;
ChemSpider	72487;
ECHA InfoCard	100.025.584
PubChem CID	80245;
UNII	NC8LG5TD4N ;
CompTox Dashboard (EPA)	DTXSID20210361 ;
	InChI InChI=1S/C4H6/c1-4-2-3-4/h1-3H2 Key: XSGHLZBESSREDT-UHFFFAOYSA-N; InChI=1/C4H6/c1-4-2-3-4/h1-3H2 Key: XSGHLZBESSREDT-UHFFFAOYAB;
	SMILES C=C1CC1;
Properties
Chemical formula	C4H6
Molar mass	54.09
Density	0.8 g/cm3
Boiling point	9 to 12 °C (48 to 54 °F; 282 to 285 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methylenecyclopropane is an organic compound with the formula (CH₂)₂C=CH₂. It is a hydrocarbon which, as the name suggests, is derived from the addition of a methylene (=CH₂) substituent to a cyclopropane ring. It is a colourless, easily condensed gas that is used as a reagent in organic synthesis.

Synthesis edit

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%)^[1] or sodium bis(trimethylsilyl)amide with further treatment by sodium tert-butoxide (yield 72%).^[2] Sodium tert-butoxide is used to isomerize byproduct 1-methylcyclopropene into methylenecyclopropane.

Reactions edit

Being a strained and unsaturated molecule methylenecyclopropane undergoes many reactions, especially in the presence of metal catalysts.^[3] For example, methylenecyclopropanes can be converted to cyclobutenes in the presence of a Platinum catalyst.^[4] This can be considered similar to the ring expansion seen in vinylcyclopropane rearrangements

Substituted methylenecyclopropanes can also be involved in trimethylenemethane cycloaddition reactions.

References edit

^ Salaun, J. R.; Champion, J.; Conia, J. M. (1977). "Cyclobutanone from Methylenecyclopropane via Oxaspiropentane". Organic Syntheses. 57: 36. doi:10.15227/orgsyn.057.0036.
^ Binger, Paul; Brinkmann, Axel; Wedemann, Petra (2002). "Highly Efficient Synthesis of Methylenecyclopropane". Synthesis (10): 1344–1346. doi:10.1055/s-2002-33122. ISSN 0039-7881.
^ Nakamura, I.; Yamamoto, Y. (2002). "Transition Metal-Catalyzed Reactions of Methylenecyclopropanes". Advanced Synthesis and Catalysis. 344 (2): 111–129. doi:10.1002/1615-4169(200202)344:2<111::AID-ADSC111>3.0.CO;2-0.
^ PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes Alois Fürstner and Christophe Aïssa J. Am. Chem. Soc.; 2006; 128(19) pp 6306 -6307; Abstract

[1] Salaun, J. R.; Champion, J.; Conia, J. M. (1977). "Cyclobutanone from Methylenecyclopropane via Oxaspiropentane". Organic Syntheses. 57: 36. doi:10.15227/orgsyn.057.0036.

[2] Binger, Paul; Brinkmann, Axel; Wedemann, Petra (2002). "Highly Efficient Synthesis of Methylenecyclopropane". Synthesis (10): 1344–1346. doi:10.1055/s-2002-33122. ISSN 0039-7881.

[3] Nakamura, I.; Yamamoto, Y. (2002). "Transition Metal-Catalyzed Reactions of Methylenecyclopropanes". Advanced Synthesis and Catalysis. 344 (2): 111–129. doi:10.1002/1615-4169(200202)344:2<111::AID-ADSC111>3.0.CO;2-0.

[4] PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes Alois Fürstner and Christophe Aïssa J. Am. Chem. Soc.; 2006; 128(19) pp 6306 -6307; Abstract

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Summary

Synthesis edit

Reactions edit

See also edit

References edit