13391-32-7Relevant articles and documents
Direct synthesis of anilines and nitrosobenzenes from phenols
St Amant,Frazier,Newmeyer,Fruehauf,Read De Alaniz
supporting information, p. 5520 - 5524 (2016/07/06)
A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.
B-Alkyl Suzuki-Miyaura cross-coupling of tri-n-alkylboranes with arylbromides bearing acidic functions under mild non-aqueous conditions
Sun, Hui-Xia,Sun, Zhi-Hua,Wang, Bing
experimental part, p. 1596 - 1599 (2009/06/18)
An efficient and chemoselective Pd-catalyzed B-alkyl Suzuki-Miyaura cross-coupling of tri-n-alkylboranes with arylbromides possessing acidic functions is described. This protocol features the relatively weak base Cs2CO3 and mild non-
Rearrangement and Cleavage of silanes by Organolithium Reagents: Conversion of Phenols into Benzylic Alcohols
Eisch, John J.,Galle, James E.,Piotrowski, Andrzej,Tsai, Miin-Rong
, p. 5051 - 5056 (2007/10/02)
The feasibility of converting phenols into their corresponding benzylic alcohols by means of novel Wittig rearrangement has been investigated.The method consists of (a) treating the phenol with (chloromethyl)trimethylsilane and base to produce the aryl (trimethylsilyl)methyl ether, (b) using sec- or n-BuLi in THF transform this ether into the α-(trimethylsilyl)benzylic alcohol, and (c) removing the silyl group with alcoholic KOH to yield the benzylic alcohol.With phenols, such as phenol itself, 2-naphthol, and 9-phenanthrol, benzylic alcohols were obtained in 50-80percent yields.Ring substituents of a nitro or methoxy type tend to favor α elimination in step b, at the expense of the Wittig rearrangement.The competitive nature of these latter two processes was examined as a function of substituents on the aryloxy groups or on the silicon, as well as a function of the lithium reagent and solvent employed.The independent synthesis and the thermal study of (phenoxymethyl)lithium demonstrated that in THF it undergoes an α elimination almost to the complete exclusion of any Wittig rearrangement.The relative importance of these two processes is discussed in terms of the locoselectivity of lithiation and an electron-transfer view of the Wittig aryl ether rearrangement.