10487-96-4Relevant articles and documents
Side Chain Hydroxylation of Aromatic Compounds by Fungi. Part 5. Exploring the Benzylic Hydroxylase of Mortierella isabellina
Holland, Herbert L.,Kindermann, Maik,Kumaresan, Sudalaiyandi,Stefanac, Tomislav
, p. 1353 - 1364 (1993)
The active site topography of the hydroxylase enzyme of Mortierella isabellina ATCC 42613, which carries out the benzylic hydroxylation of toluene, ethylbenzene, and related compounds, has been explored.Operating in a whole cell biotransformation mode, this enzyme shows selectivity in substrate processing based on the nature, position and size of substituent side chains close to the site of hydroxylation.The results of determination of the yield and stereochemistry of hydroxylation of over twenty substrates and potential substrates, together with previously reported data, have been used to propose an active site model for the benzylic hydroxylase enzyme.
13C NMR spectroscopic comparison of sterically stabilized meta and para-substituted o-tolyldi(adamant-l-yl)methyl cations with conjugatively stabilized benzyl cations
Lomas, John S.
, p. 2601 - 2609 (1996)
A series of meta- and para-substituted anti-o-tolyldi(adamant-1-yl)methyl cations has been generated by reaction of anti-o-tolyldi(adamant-1-yl)methanols with trifluoroacetic acid in chloroform. 13C NMR spectroscopy indicates small but significant variations in the chemical shifts of the charged carbon and its nearest neighbours on the adamantyl groups, and departures from additivity of substituent effects on the shifts of the aromatic carbons. Previous work on the closely related di(adamant-1-yl)benzyl cations is discussed. Comparison with data on aryl-substituted carbocations in superacid media reveals marked differences in the aromatic carbon shifts in the two types of carbocation. The dihedral angle between aryl and carbocation planes in aryldi(adamant-1-yl)methyl cations is estimated to be about 60°.
Electrophotochemical Ring-Opening Bromination oftert-Cycloalkanols
Yamamoto, Kosuke,Toguchi, Hiroyuki,Kuriyama, Masami,Watanabe, Shin,Iwasaki, Fumiaki,Onomura, Osamu
, p. 16177 - 16186 (2021/09/13)
An electrophotochemical ring-opening bromination of unstrainedtert-cycloalkanols has been developed. This electrophotochemical method enables the oxidative transformation of cycloalkanols with 5- to 7-membered rings into synthetically useful ω-bromoketones without the use of chemical oxidants or transition-metal catalysts. Alkoxy radical species would be key intermediates in the present transformation, which generate through homolysis of the O-Br bond in hypobromite intermediates under visible light irradiation.
Cu-Catalyzed: O -alkylation of phenol derivatives with alkylsilyl peroxides
Sakurai, Shunya,Kano, Taichi,Maruoka, Keiji
supporting information, p. 81 - 84 (2021/01/14)
A Cu-catalyzed O-alkylation of phenol derivatives using alkylsilyl peroxides as alkyl radical precursors is described. The reaction proceeds smoothly under mild reaction conditions and the use of two different ligands with a Cu catalyst provides a wide range of products. A mechanistic study suggested that the reaction proceeds via a radical mechanism. This journal is