445251-38-7

Upstream product

• 78-92-2 iso-butanol 
• 100-51-6 benzyl alcohol 
• 74-88-4 methyl iodide 
• 100-42-5 styrene 
• 1517-69-7 (R)-1-phenylethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 98-86-2 acetophenone 
• 78-93-3 butanone 
• 98-85-1 1-Phenylethanol 

Relevant academic research and scientific papers

Does a chiral alcohol really racemize when its OH group is protected with Boyer's reaction?

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.

BiBr3-catalyzed benzylation of alcohols. Stereochemistry and mechanistic investigations

We have investigated the benzylation of optically active aliphatic alcohols (octan-2-ol and butan-2-ol) as well as cis and trans 2-methylcyclohexanol or (S)-(-)-menthol, catalyzed by bismuth (III) bromide in the presence of (-) or (±)-1-phenylethanol (PeOH). Under mild conditions, aliphatic alcohols provided an equimolar mixture of diastereomeric ethers while alicyclic alcohols gave rise to ethers with retention of configuration. To explain these results, we assumed that BiBr3, acting as Lewis acid, would lead to the formation of a 6-fold coordinated bismuth intermediate involving two molecules of 1-phenylethanol and one molecule of aliphatic alcohol. We have proposed a mechanism to explain these BiBr3-promoted etherification reactions.

Chemical equilibrium study in the reacting system of (1-alkoxyethyl)benzene synthesis from isoalkanols and styrene

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

Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp2)-H and C(sp3)-O Bonds

A novel cobalt-catalyzed C-H alkylation of arenes and olefins is achieved with (pyridin-2-yl)isopropyl amine as an N,N-bidentate directing group. Different linear, branched, and cyclic alkyl ethers were used as practical secondary alkylating reagents through cleavage of C(sp3)-O bond, providing an efficient approach to the synthesis of verstile o-alkylated arylamides and tetrasubstituted acrylamides. Mechanistic studies indicate that cleavage of the inert C(sp3)-O bond involves a cobalt-promoted radical process and that cleavage of the inert C(sp2)-H bond by a cobalt catalyst is a rate-limiting step.

Efficient addition of alcohols, amines and phenol to unactivated alkenes by AuIII or PdII stabilized by CuCl2

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.

Effective Au(III)-CuCl2-catalyzed addition of alcohols to alkenes

Alkenes can be activated by Au(III) catalysts, and the effective addition of alcohols to alkenes can be carried out under mild conditions with Au(III), provided that catalytic amounts of CuCl2 are added, which significantly stabilize the cationic Au(III). The Royal Society of Chemistry.

Vapor pressures and enthalpies of vaporization of benzyl halides and benzyl ethers

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.

BiBr3, an efficient catalyst for the benzylation of alcohols: 2-Phenyl- 2-propyl, a new benzyl-type protecting group

The benzylation of aliphatic alcohols with various benzylic alcohols has been achieved in the presence of BiBr3 under mild conditions. 2- Phenylpropan-2-ol proved to be the most efficient and can be considered as a novel protecting group. (C) 2000 Elsevier Science Ltd.

Elaboration of α-Substituted Benzyl Ethers and Sulphides by Suppression of the Wittig and Related Rearrangements

Co-ordination of benzyl alkyl ethers and sulphides to chromium tricarbonyl allows α-substitution via the corresponding α-carbanions to be achieved by suppression of the Wittig and related rearrangements.