Methylenecyclohexane (IUPAC name: methylidenecyclohexane) is an organic compound with the molecular formula C7H12.
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| Preferred IUPAC name
Methylidenecyclohexane | |
| Other names
Methylenecyclohexane
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3D model (JSmol)
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| ECHA InfoCard | 100.013.412 |
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CompTox Dashboard (EPA)
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| Properties | |
| C7H12 | |
| Molar mass | 96.170 g/mol |
| Boiling point | 102 to 103 °C (216 to 217 °F; 375 to 376 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis edit
It can be produced by a Wittig reaction or a reaction with a Tebbe's reagent from cyclohexanone.[1][2][3] It can also be synthesized as a side product of the dehydration of 2-methylcyclohexanol into 1-methylcyclohexene.
Structure edit
Methylenecyclohexane is an unsaturated hydrocarbon, containing a cyclohexane ring with a methylene (methylidine) group attached.
See also edit
References edit
- ^ Wittig, George; Schoellkopf, U. (1960). "Methylenecyclohexane". Organic Syntheses. 40: 66. doi:10.15227/orgsyn.040.0066.
- ^ Mark, Herman F. (2007). Encyclopedia of Polymer Science and Technology, Concise. Hoboken, New Jersey: John Wiley & Sons. p. 682. ISBN 978-0-470-04610-4.
I this way, cyclohexanone is transformed into methylenecyclohexene and benzaldehyde into stryene.
- ^ Dalton, David R. (August 4, 2011). Foundations of Organic Chemistry: Unity and Diversity of Structures, Pathways, and Reactions. John Wiley & Sons. pp. 819–820. ISBN 978-1-118-00538-5.
Now, when cyclohexanone is added to the solution in which the [Tebbe] reagent has been generated, reaction occurs to produce methylenecyclohexane and triphenylphosphine oxide