137445-37-5Relevant academic research and scientific papers
A new route for the preparation of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene using Friedel-Crafts intramolecular cyclobenzylation
Yamato,Fukumoto,Sakaue,Furusawa,Tashiro
, p. 699 - 700 (1991)
A convenient preparation of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene based on a novel Friedel-Crafts intramolecular cyclobenzylation, involving five steps from 1,2-diphenylethane, is described.
Selective Preparation of Polycyclic Aromatic Hydrocarbons. Part 7. A Preparative Route to 10,11-Dihydro-5H-dibenzo-cycloheptenes Using Friedel-Crafts Intramolecular Cyclobenzylation
Yamato, Takehiko,Sakaue, Naozumi,Komine, Masayasu,Nagano, Yoshiaki
, p. 1708 - 1735 (2007/10/03)
Cyclobenzylation of 2-hydroxymethyldiphenylethanes 4 and 2,2'-bis(hydroxymethyl)diphenylethanes 13 in the presence of a solid perfluorinated sulfonic acid resin, Nafion-H, as a catalyst results in novel polycyclic aromatic hydrocarbons, dibenzocyclopentenes.Dibenzocyclopentenes were also prepared from diphenylethanes by a benzylation reaction, which incorporates chloromethylation of a hydrocarbon followed by Friedel-Crafts intramolecular cyclization reaction.The present method involving the action of ClCH2OMe and TiCl4 on a variety of diphenylethanes (constructed such that electrophilic substitution occurs ortho to the diphenylethane linkage) offers a convenient, mild one-pot synthesis of substituted dibenzocycloheptenes.The mechanism of these reactions is also discussed.
