33925-52-9

Upstream product

• 881-42-5 diphenylmethyllithium 
• 106-95-6 allyl bromide 
• 91-01-0 1,1-Diphenylmethanol 
• 18292-38-1 2-methallyltrimethylsilane 
• 86-29-3 Diphenylacetonitrile 
• 18292-39-2 (2-methyl-1-propen-1-yl)trimethylsilane 
• 954-67-6 benzhydryl acetate 
• 75-65-0 tert-butyl alcohol 
• 84803-28-1 2-chloro-2-methyl-4-4-diphenylbutane 
• 33925-51-8 2,2-diphenyl-4-methyl-4-pentenenitrile 

Downstream Products

• 102434-99-1 3-Chlor-3-methyl-1,1,5,5-tetraphenylpentan 

Relevant academic research and scientific papers

Beyond the Tebbe Olefination: Direct Transformation of Esters into Ketones or Alkenes

A direct, effective, and operationally simple transformation of esters into ketones or alkenes by the exclusive action of Tebbe's reagent has been developed. The transformation utilizes the dual character of Tebbe's reagent as both a methylenation agent and a rearrangement catalyst in the reaction of a wide range of substituted vinyl ethers. The resulting transformation involves sequential methylenation and rearrangement reactions and it offers a high degree of selectivity toward the synthesis of ketones or alkenes. The scope and limitations of the developed methods have been also examined.

Direct Synthesis of Indanes via Iron-Catalyzed Dehydrative Coupling/Friedel–Crafts Cyclization of Two Different Alcohols

We report herein a novel iron-catalyzed cascade dehydrative coupling/Friedel–Crafts cyclization of two different alcohols, providing a variety of indanes, which are ubiquitous substructures found in natural products, pharmaceuticals, and functional materi

Carbenium ion formation by fragmentation of electrochemically generated oxonium ions

Fragmentation of electrochemically generated oxonium ions can be exploited to form carbenium ions at a low oxidation potential in the presence of a nucleophile. The application of this concept is demonstrated for the allylation of carbenium ions generated by the anodic oxidation of stannylmethylethers.

Direct coupling of alcohols with alkenylsilanes catalyzed by indium trichloride or bismuth tribromide

Indium halides or bismuth halides catalyzed the coupling of various alcohols with alkenylsilanes to give the corresponding alkenes stereospecifically without any other activators. The Royal Society of Chemistry 2008.

Direct coupling reaction between alcohols and silyl compounds: Enhancement of Lewis acidity of Me3SiBr using InCl3

The combination of InCl3 and Me3SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced Lewis acidity of this system was measured by the 13C NMR in terms of the coordination to an alcohol. Moreover, the interaction between Me3SiBr and the In(III) species was revealed by 29Si NMR spectral analysis. Highly chemoselective allylations toward a hydroxyl moiety over ketone and acetoxy ones have been demonstrated.

Iron-Mediated C-C Bond Formation. Preparation of (Trimethylenemethane)iron Complexes via Reaction of Weak Carbon Nucleophiles with in Situ Generated Cross-Conjugated Pentadienyl Cations. Nucleophilic Attack on (Trimethylenemethane)iron Complexes with Carbanions

The reaction of (2-(acetoxymethylene)-1,3-butadiene)Fe(CO)3 (8) or ((acetoxymethylene)trimethylenemethane)Fe(CO)3 (9) with weak carbon nucleophiles in the presence of BF3*Et2O gives the corresponding substituted (trimethylenemethane)Fe(CO)3 complexes as the major product.Applicable nucleophiles include trialkylaluminums, allyltrimethylsilane, and 2-((trimethylsilyl)oxy)-1-propene.This reaction proceeds in a stereospecific fashion; reaction of 1 2 gives a single (trimethylenemethane)iron product.The reaction of (1,2-bis(acetoxymethylene)-1,3-butadiene)Fe(CO)3 (20) with allyltrimethylsilane gives a (TMM(Fe(CO)3 product in which two new C-C bonds have been formed in one reaction.Reaction of TMMFe(CO)3 (1a) and substituted derivatives with carbanions, followed by workup with trifluoroacetic acid, gives the corresponding methallylated product.Applicable nucleophiles include anions derived from diphenylmethane, ethyl isobutyrate, isobutylnitrile, and 2-phenyl-1,3-dithiane.Use of allyl bromide in place of trifluoroacetic acid gives 6-substituted 5-methylene-1-hexenes as products, the result of the three-component coupling.

Nucleophilic addition to coordinated polyenes: A novel method for the liberation of the trimethylenemethane ligand involving C-C bond formation

Reaction of (trimethylenemethane)Fe(CO)3 with carbon nucleophiles, followed by protonation yields the corresponding methallylated nucleophile in good yield. Products which incorporate carbonyl ligands are also observed.

Relative Reactivities of Alkyl-Substituted Alkenes and Cycloalkenes towards Diarylcarbenium Ions

The relative reactivities of alkyl-substituted alkenes 4 towards diarylmethyl cations 2 generated in situ from diarylmethyl chlorides 1 and Lewis acids were determined by competition experiments.The relative reactivities were almost independent of the nature of the Lewis acid. Eventual differences of the solvation free enthalpies of various activated complexes are, therefore, independent of the nature of the gegen ions.The rate acceleration by methyl groups - 6-50 by CH3 at the attacked vinylic position and approximately 104 at the developing carbenium centre - indicates a scarcely bridged transition state.