75245-67-9

Upstream product

• 1589-82-8 phenylmagnesium bromide 
• 97-62-1 Ethyl isobutyrate 
• 547-63-7 Methyl isobutyrate 
• 100-44-7 benzyl chloride 
• 920-39-8 isopropylmagnesium bromide 
• 102-04-5 1,3-Diphenylpropanone 
• 100-39-0 benzyl bromide 
• 1068-55-9 isopropylmagnesium chloride 

Downstream Products

• 74202-34-9 (E)-2-Benzyl-3-methyl-1-phenyl-1-buten 
• 74202-33-8 (Z)-2-Benzyl-3-methyl-1-phenyl-1-buten 
• 64278-89-3 4-methyl-1,2-diphenylpentan-3-one 
• 857824-87-4 2-benzyl-2-isopropyl-3-phenyl-oxirane 

Relevant academic research and scientific papers

Development of a Scalable Lanthanide Halide/Quaternary Ammonium Salt System for the Nucleophilic Addition of Grignard Reagents to Carbonyl Groups and Application to the Synthesis of a Remdesivir Intermediate

This manuscript describes the development and implementation of a scalable additive system, consisting of a lanthanide salt and a solubilizing quaternary ammonium salt, to improve the yield and robustness of the addition of an organomagnesium reagent to a

LaCl3·2LiCl-catalyzed addition of Grignard reagents to ketones

The addition of Grignard reagents to ketones using substoichiometric amounts of LaCl3·2LiCl was studied. Catalytic amounts of LaCl3·2LiCl (30 mol%) provide, in most cases, yields similar to those obtained using a stoichiometric amoun

Solutions of anhydrous lanthanide salts and its preparation

The present invention relates to anhydrous solutions of MX 3 €￠z LiA in a solvent, wherein M is a lanthanide including lanthanum, or yttrium or indium; z > 0; and X and A are independently or both monovalent anions, preferably Cl, Br or I. The solution is readily prepared by dissolving or suspending MX 3 or its hydrate and z equiv LiA in water or hydrophilic solvents, or mixtures thereof, removing the solvent under vacuum and dissolving the resulting powder in another solvent. The solution of MX 3 €￠z LiA can advantageously be used e.g. in addition reactions of Grignard reagents to ketones and imines. Even the catalytic use of MX 3 €￠z LiA is possible. Also claimed are a method for preparing the anhydrous solutions, the use of such solution in a chemical reaction and chemical compositions MX 3 €￠z LiA, with M, z, X and A as indicated above.

Soluble lanthanide salts (LnCl3,·2 LiCl) for the improved addition of organomagnesium reagents to carbonyl compounds

(Chemical Equation Presented) Easy-to-prepare solutions of LnCl 3·2 LiCl (Ln = La, Ce, Nd) (0.3-0.5 M in THF) are a unique source of soluble lanthanide salts with versatile applications in organic synthesis. These salts can serve as promoters or catalysts for the addition of organometallic compounds to sterically hindered, enolizable or α,β-unsaturated ketones or imines.

Some uses of mischmetall in organic synthesis

Mischmetall, an alloy of the light lanthanides, has been used in a variety of organic reactions, either as a coreductant in samarium(II)-mediated reactions (Barbier and Grignard-type reactions, pinacolic coupling reactions) or as the promoter of Reformatsky-type reactions. It has been also employed as the starting material for easy syntheses of lanthanide trihalides, the reactivity of which has been explored in Imamoto and Luche-Fukuzawa reactions and in Mukaiyama aldol reactions.

Conformations and Rotational Barriers of 1,3-Diphenylallyllithium Compounds

The phenyl substituents of the 1,3-diphenylallyl anions 10 (gegenion lithium, solvent tetrahydrofuran) can exist in the exo,exo-, endo,exo- and/or endo,endo-conformations.We have investigated the influence of substituents R at C2 on the equilibria of these solvent separated ion pairs.While 10a (R = H) is the only one to exist predominantly in the exo,exo-conformation, and in 10b and c (R = CH3 and CN, respectively) the endo,exo-conformers predominate, in 10d, e and f (R = C2H5, C6H5 and iPr, respectively) there is increasing preference for the endo,endo-conformation, which in 10g (R = tBu) is the dominant (>/= 95percent) conformation.A vast congestion in the endo,endo-conformation is avoided by a rotation of the phenyl rings out of the plane of the allyl carbon atoms, and an expansion of the sp2 angles in the allyl moiety.The rotational barriers around the allyl anion bonds decrease from 19.1 kcal*mol-1 (10a) to 12.5 kcal*mol-1 (10f).Since this trend parallels to the above mentioned shift of the equilibria, it is due to ground state effects.The rotational barriers are only slightly (10a,b) if at all influenced by gegenion effects, which is in sharp contrast to the parent allyl "anion".Therefore, the rotational barriers of the allyl anions 10 are qualified for a comparison with the corresponding radicals and cations.Furthermore, with ΔG(excit)273 deg C = 19.1 kcal*mol-1 as a lower limit value for the rotational barrier of the parent allyl anion, one can estimate that the true value of this species must be close to barriers calculated with STO-3G and 4-3l-G programs (ca. 26 kcal*mol-1).