445251-38-7Relevant articles and documents
Does a chiral alcohol really racemize when its OH group is protected with Boyer's reaction?
Fraschetti, Caterina,Speranza, Maurizio,Filippi, Antonello
, p. 88 - 91 (2010)
Chiral reactants have been employed for assessing the real stereochemistry of the BiBr3-catalyzed synthesis of benzylic ethers, a very useful reaction for protecting alcoholic groups. The results of this investigation are in clear contrast with the conclusions of previous studies (Boyer et al., Tetrahedron 2001;57:1917-1921). Indeed, chiral GC-MS analysis of the ethereal products gives unequivocal evidence of the complete racemization of the benzylic moiety and the complete retention of configuration of the protected alcoholic substrate. Such findings make BiBr3 a powerful and stereochemically preservative catalyst for benzylation of chiral alcohols, and a potential candidate for orthogonal protecting group strategies applicable to polyhydroxy compounds.
Chemical equilibrium study in the reacting system of (1-alkoxyethyl)benzene synthesis from isoalkanols and styrene
Verevkin, Sergey P.,Heintz, Andreas
, p. 728 - 733 (2002)
The chemical equilibrium of the reactive systems isoalkanol + styrene ? (1-alkoxyethyl)benzene (alkyl is isopropyl, sec-butyl, and cyclohexyl) was studied in the liquid phase in the temperature range 343 to 433 K using a cation exchanger as heterogeneous
Efficient addition of alcohols, amines and phenol to unactivated alkenes by AuIII or PdII stabilized by CuCl2
Zhang, Xin,Corma, Avelino
, p. 397 - 403 (2008/09/17)
The nucleophilic addition of alcohols, amines and phenol to unactivated alkenes catalyzed by cationic gold and palladium becomes limited due to the fast reduction into metallic gold under reaction conditions. The presence of CuCl2 retards the reduction of AuIII and PdII, strongly increasing the turnover number of gold and palladium catalysts. It is shown that new AuIII-CuCl2 and PdII-CuCl 2 catalysts are active and selective for the nucleophilic addition of alcohols, amines and phenol to unactivated alkenes. This journal is The Royal Society of Chemistry.
Vapor pressures and enthalpies of vaporization of benzyl halides and benzyl ethers
Krasnykh, Eugen L.,Vasiltsova, Tatiana V.,Verevkin, Sergey P.,Heintz, Andreas
, p. 1372 - 1378 (2007/10/03)
Molar enthalpies of vaporization ΔlgHmo of seven benzyl halides and seven benzyl ethers have been obtained from the temperature dependence of the vapor pressure measured by the transpiration method. These values and the correlation-gas chromatography method, based on Kovat's index, have been applied for the determination of ΔlgHmo of three cumyl halides (Cl, Br, and I). The data obtained for ΔlgHmo of benzyl derivatives have been checked successfully for internal consistency using enthalpies of formation of alkyl halides and alkyl ethers available from the literature.