104892-58-2Relevant academic research and scientific papers
Remote electronic effects in the rhodium-catalyzed nucleophilic ring opening of oxabenzonorbornadienes.
Lautens, Mark,Schmid, Gavin A,Chau, Anh
, p. 8043 - 8053 (2007/10/03)
We report the application of our rhodium-catalyzed nucleophilic ring-opening methodology to unsymmetrically arene-substituted oxabenzonorbornadienes. The regioselectivity of the ring opening was investigated using a variety of nucleophiles that led to a broad selection of dihydronaphthalene products. It was found that good to excellent regioselectivities are obtained using strongly pi-donating substituents, whereas sigma-donating and electron-withdrawing functionalities have a minimal effect. Post ring-opening manipulations of functional groups in the dihydronaphthalene products were shown to give efficient access to mono- and diamine tetrahydronaphthalene building blocks.
PREPARATION OF DEUTERIATED 1-PHENYLETHANOLS BY REDUCTIVE DEHALOGENATION OF THE CORRESPONDING HALOGENOACETOPHENONES WITH RANEY ALLOYS IN AN ALKALINE DEUTERIUM OXIDE SOLUTION
Tashiro, Masashi,Mataka, Shuntaro,Nakamura, Hiroshi,Nakayama, Kouji
, p. 179 - 182 (2007/10/02)
Deuteriated 1-phenylethanols were prepared by reductive dehalogenation of the corresponding halogenoacetophenones with Raney Ni-Al and Cu-Al alloys in 5percent NaOD-D2O solution.It was found that the Ni-Al alloy introduced greater than expected numbers of deuterium atoms in the phenyl ring, but the expected deuteriated 1-phenylethanols were obtained in high yield and in high isotopic purity when Raney Cu-Al alloy was used.
