68846-65-1

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 2223, 1982 DOI: 10.1016/S0040-4039(00)87306-2

InChI:InChI=1/C10H10/c1-8-6-9-4-2-3-5-10(9)7-8/h2-5H,1,6-7H2

Upstream product

• 29817-09-2 1-methylene-2-phenylcyclopropane 
• 15677-15-3 benzo[2,3]bicyclo[3.1.0]hexane 
• 120906-16-3 1-allyl-2-(bromomethyl)benzene 
• 120906-17-4 1-allyl-2-(iodomethyl)benzene 
• 75-09-2 dichloromethane 
• 615-13-4 2-indanone 
• 89121-39-1 1-allyl-2-(chloromethyl)benzene 

Downstream Products

• 5445-45-4 2-(hydroxymethyl)indan 
• 2177-47-1 2-Methylindene 

Relevant academic research and scientific papers

Dichloromethane activation. Direct methylenation of ketones and aldehydes with CH2Cl2 promoted by Mg/TiCl4/THF

(Chemical Equation Presented) This Mg-TiCl4-promoted CH 2-transfer reaction of CH2Cl2 represents an extremely simple, practical, and efficient methylenation of a variety of ketones and aldehydes, especially in enolizable or sterically hindered ketones such as 2,2-dimethylcyclohexanone, camphor, and fenchone.

Energy Well of the Orthogonal Trimethylenemethane. - 1-Methylene-2-phenylcyclopropane Thermolysis

From the heat of hydrogenation of 5, the activation enthalpy for the racemization of the title compound, and the oxygen dependance of the trapping rate of the intermediate diradical 8 the energy profile for the degenerate methylene-cyclopropane rearrangement can be constructed, which leads to heats of formation for the triplet and singlet state of the diradical 8 of ΔHf0 93.9 and 95.6 kcal mol-1, respectively. - Key Words: Diradicals / Oxygen trapping / Energy well / Heat of formation / Heat of hydrogenation

Palladium-Catalyzed Cyclization of Benzyl Halides and Related Electrophiles Containing Alkenes and Alkynes as a Novel Route to Carbocycles

Treatment of benzyl halides and related electrophiles containing alkene and alkyne groups with a catalytic amount of Pd complexes, such as Pd(PPh3)4, provides the corresponding cyclization products containing five- through seven-membered rings often with retention of the alkene regiochemistry.

Thermochemistry of Phenyl-Substituted Benzobicyclohex-2-enes

The thermal rearrangements of benzobicyclohex-2-ene (21) and its phenyl-substituted analogues 22-25 (Scheme V) as models of sterically constrained phenylcyclopropanes have been studied by means of flash vacuum pyrolysis.In most cases the major pathway was cleavage of the "internal" C(1)-C(5) cyclopropane bond followed by a 1,2-hydrogen or a 1,2-phenylshift in the resulting biradical.For 6-phenylbenzobicyclohex-2-ene (25), substantial cleavage of the "external" C(1)-C(6) cyclopropane bond was observed, the phenyl substitution pattern being favorable for stabilization of the resulting biradical 62.Phenyl-substituted 1,2-dihydronaphthalenes 44, 47, 51, and 55 are among the major products.Comparison of the plots of the pyrolysis product composition of the 1,2-dihydronaphthalenes vs. pyrolysis temperature with similar plots of the title compounds (22-25) suggested that some of the minor products, viz., the 1,2-divinylbenzenes 31, 42, and 49, are formed via carbenes 30, 41, 50, 57, and 61 rather than via biradicals.Especially at higher pyrolysis temperatures, a large amount of an oxidation product, viz., 1- or 2-phenylnaphthalene (48 or 54), is formed.