439134-46-0Relevant articles and documents
Competing Regiochemical Pathways in the Heck Arylation of 1,2-Dihydronaphthalene
Maeda, Kenji,Farrington, Edward J.,Galardon, Erwan,John, Benjamin D.,Brown, John M.
, p. 104 - 109 (2002)
The Heck reaction of aryl iodides with 1,2-dihydronaphthalene has been examined. Two separate reaction pathways are observed under all the conditions tried. Arylation adjacent to the aromatic ring leads to a subsequent double bond shift such that the product is a 1-aryl-1,2-dihydronaphthalene. The alternative regiochemistry leads to production of the corresponding 3-aryl-1,2-dihydronaphthalene, and labelling studies with specifically deuterated alkenes demonstrate that this is most likely to be the result of a trans Pd-H elimination pathway. The ratio always varies between 75:25 in favour of the 3-aryl product (Jeffery conditions) to 70:30 in favour of the 1-aryl product.
Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: A diastereoselective total synthesis of (±)-indatraline
Silva Jr., Luiz F.,Siqueira, Fernanda A.,Pedrozo, Eliane C.,Vieira, Fabiana Y. M.,Doriguetto, Antonio C.
, p. 1433 - 1436 (2008/02/02)
Equation presented A new approach for the synthesis of (±)- indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by Phl(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.
