41158-41-2

Basic information

• Product Name: 2-Methyl methylenecyclopentane
• Synonyms: 2-Methyl methylenecyclopentane;1-Methyl-2-methylenecyclopentane
• CAS NO: 41158-41-2
• Molecular Formula: C₇H₁₂
• Molecular Weight: 96.17
• Mol File: 41158-41-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Methyl methylenecyclopentane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl methylenecyclopentane(41158-41-2)
• EPA Substance Registry System: 2-Methyl methylenecyclopentane(41158-41-2)

Safety Data

• Hazardous Substances Data: 41158-41-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 647, 1981 DOI: 10.1021/jo00316a038

Upstream product

• 56404-39-8 (+/-)-1-r-acetoxy-1,2c-dimethyl-cyclopentane 
• 56404-39-8 (+/-)-1-r-acetoxy-1,2t-dimethyl-cyclopentane 
• 109577-27-7 1-Bromomethyl-2-methylene-cyclopentane 
• 86365-78-8 2-bromo-1,6-heptadiene 
• 1009634-44-9 1-[2-(bicyclo[3.1.0]hexan-1-yl)acetoxy]-2(1H)-pyridinethione 
• 90245-62-8 WCl₂(PMePh₂)4 
• 21889-88-3 hept-6-en-2-one 
• 67-56-1 methanol 

Downstream Products

• 73803-82-4 (2-Methylcyclopentyl)methanol 
• 116530-98-4 (+/-)-(cis-2-methyl-cyclopentyl)-acetic acid 
• 116530-98-4 (trans-2-methylcyclopentyl)acetic acid 

Relevant articles and documents

Effect of ketene additive and Si/Al ratio on the reaction of methanol over HZSM-5 catalysts

The influence of ketene as possible intermediate for the reaction of methanol to aromatics was investigated over HZSM-5 catalysts (Si/Al ratio of 15 and 9) using diketene-acetone (2,2,6-trimethyl-4H-1,3-dioxin-4-one) as ketene precursor under atmospheric

Deoxygenative coupling of ketones and alkenes by tungsten(II) compounds

Tungsten(II) compounds such as WCl2(PMePh2)4 (1) react with acetone and ethylene to give a good yield of the tungsten(IV)-oxo complexes W(O)(CH2=CH2)Cl2(PMePh2)2 (4) and a moderate amount of 3-methyl-1-butene. Cyclopentanone and ethylene plus 1 yield 4 and vinylcyclopentane; methyl vinyl ketone and ethylene give 4 and 3-methyl-1,4-pentadiene. The reaction of cyclopentanone and propylene with 1 yields a small amount of 2-cyclopentylpropene. Intramolecular deoxygenative coupling occurs with 6- and 7-en-2-ones to form 1-methyl-2-methylene-substituted cyclopentyl and cyclohexyl ring systems, respectively. The net result of these reactions is transfer of the ketone oxygen atom to tungsten, accompanied with its replacement by a hydrogen and a vinyl group. The suggested mechanism for this deoxygenative coupling (Scheme I) is coordination of both the ketone and ethylene to tungsten, coupling to form a 2-oxametallacyclopentane, β-hydrogen elimination to an allyloxy hydride species, C-O bond cleavage to an oxo allyl hydride complex, and reductive elimination of alkene. Consistent with the suggestion of an oxametallacycle, hydrolysis of the reaction mixture of 1 and 6-hepten-2-one provides stereospecifically trans-1,2-dimethylcyclopentanol. The enones methyl vinyl ketone and 5-hexen-2-one react with 1 to form stable complexes in which the enone is bound in an η4 fashion, similar to the proposed mixed alkene ketone intermediates in the coupling reactions. A related tungsten(II) butadiene complex, WCl2(CH2= CHCH=CH2) (PMePh2)2, has also been isolated.