109030-55-9Relevant academic research and scientific papers
Iron-Catalyzed Ortho C-H Homoallylation of Aromatic Ketones with Methylenecyclopropanes
Kimura, Naoki,Katta, Shiori,Kitazawa, Yoichi,Kochi, Takuya,Kakiuchi, Fumitoshi
, p. 4543 - 4549 (2021/04/07)
We report here a C-H homoallylation reaction of aromatic ketones with methylenecyclopropanes (MCPs) only using a catalytic amount of Fe(PMe3)4. A variety of aromatic ketones and MCPs are applicable to the reaction to form ortho-homoallylated aromatic ketones selectively via regioselective scission of the three-membered rings. The homoallylated products are amenable to further elaborations, providing functionalized 1,2-dihydronaphthalenes.
The photochemical rearrangement of 1,2-dihydronaphthalenes into 1,4-dihydronaphthalenes induced by amines
Cuppen, Th. J. H. M.,Berendsen, N.,Laarhoven, W. H.
, p. 168 - 171 (2007/10/02)
The synthetic usefulness of the deprotonation/protonation reaction of excited 1,2-dihydronaphthalenes into 1,4-dihydronaphthalenes induced by amines has been investigated using 13 different substituted 1,2-dihydronaphthalenes and related compounds.The yield of the rearrangement ranges from 5 to 96percent.The formation of side-products depends on the position of protons in the substrate, which can be abstracted by the amine, and on competitive photoreactions.
Photochemistry of 3-methyl-1,2-dihydronaphthalene
Laarhoven, W. H.,Berendsen, N.
, p. 367 - 371 (2007/10/02)
Irradiation of the title compound (6) with a broad spectrum lamp at room temperature afforded 2-methylidene-1,2,3,4-tetrahydronaphthalene(8) and 2-methylnaphthalene (7).Apart from 8, irradiation of 6 at -45 deg also afforded 5-methylbenzobicyclohex-2-ene (12) 1-methylidene-2-(2-tolyl)cyclopropane (13) as well as a small amount of 2-methyl-1,4-dihydronaphthalene (14).Both 12 and 13 originate from the ring-opened product of 6.Compound 14 is probably formed via a retro di-?-methane rearrangement from 12.Irradiation of 6 in n-propylamine afford the same photoproducts, 14 being the main one in this case.
