66129-95-1

Upstream product

• 37064-20-3 2-methylpropyl ester butanoic acid 
• 128742-43-8 1,1-diphenylspiro[2.2]pentane 
• 119-61-9 benzophenone 
• 66130-01-6 2-methyl-1,1-diphenylbutan-1-ol 
• 624-64-6 trans-2-Butene 
• 90-99-3 diphenylchloromethane 
• 590-18-1 (Z)-2-Butene 

Downstream Products

• 309978-20-9 (C₆H₅)2CHCH(CH₃)CHCH₃BH₂ 
• 26465-78-1 (2-methylbutane-1,1-diyl)dibenzene 
• 83289-87-6 2-methyl-1,2-diphenyl-1-butanone 
• 79239-04-6 3,3-diphenyl-2-ethylpropene 
• 111550-98-2 1,1-diphenyl-2-methyl-2-butene 

Relevant academic research and scientific papers

Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins

Asymmetric hydrogenation has evolved as one of the most powerful tools to construct stereocenters. However, the asymmetric hydrogenation of unfunctionalized tetrasubstituted acyclic olefins remains the pinnacle of asymmetric synthesis and an unsolved challenge. We report herein the discovery of an iridium catalyst for the first, generally applicable, highly enantio- and diastereoselective hydrogenation of such olefins and the mechanistic insights of the reaction. The power of this chemistry is demonstrated by the successful hydrogenation of a wide variety of electronically and sterically diverse olefins in excellent yield and high enantio- and diastereoselectivity.

Polylithiumorganic compounds. Part 29: C,C Bond cleavage of phenyl substituted and strained carbocycles using lithium metal

The reaction of phenyl substituted cyclopropanes phenylcyclopropane and 1,1-diphenylcyclopropane, phenyl substituted bicyclobutanes 1- phenylbicyclobutane, 1-methyl-3-phenylbicyclobutane, 1-methyl-2,2- diphenylbicyclobutane, as well as phenyl substituted spiropentanes phenylspiropentane and 1,1-diphenylspiropentane with lithium metal or lithium di-t-butylbiphenyl (LiDBB) was investigated. Under suitable reaction conditions and choice of solvent in all cases cleavage of the single bond next to the activating phenyl group was observed. The dilithiumorganic compounds thus obtained are sufficiently stable and can be trapped with electrophiles. Lithium hydride elimination is observed as follow-up reaction only in a few cases. The corresponding anions of the strained ring systems 1-lithio-2,2- diphenylcyclopropane, 1-lithio-3-phenylbicyclobutane, 1-lithio-3-methyl-2,2- diphenylbicyclobutane, and 1-lithio-4-phenylspiropentane, which can be obtained by lithium bromine exchange or by metalation of the unsubstituted carbocycle, do not show any cleavage upon reaction with lithium metal. The reaction of phenyl substituted cyclopropanes, bicyclobutanes as well as spiropentanes with lithium metal with formation of highly reactive dilithiumorganic compounds was investigated. In all cases cleavage of the bond next to the phenyl substituent(s) was 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.

RELATIVE REACTIVITIES OF ALKENES TOWARD THE DIPHENYLMETHYL CATION

The relative reactivities of alkyl and phenyl substituted alkenes toward diphenylmethyl chloride/ZnCl2/Et2O in dichloromethane at -78 deg C have been determined by competition experiments.The transition state structure is discussed.