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• 38023-36-8 1,4-diphenyl-2,3-dimethylbutadiene-1,3 
• 300-57-2 allylbenzene 
• 873-49-4 cyclopropylbenzene 
• 74707-05-4 2,5-dibromo-3,4-dimethylthiophene 
• 6921-34-2 benzylmagnesium chloride 
• 62640-71-5 2,3-dimethyl-1,4-diphenylbutane-2,3-diol 
• 31731-87-0 1-methyl-2-phenylethylmagnesium bromide 
• 626-87-9 1,4-dibromopentane 
• 6940-78-9 4-chlorobutyl bromide 
• 71-43-2 benzene 
• 637-50-3 1-phenylpropene 
• 74714-05-9 3,4-dibenzylthiophene 
• 2114-39-8 (2-bromopropyl)-benzene 
• 2327-99-3 1-phenylpropadiene 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling of functionalized alkyl halides and tosylates with secondary and tertiary alkyl Grignard reagents

Added value: A copper-based method is highly efficient for the cross-coupling of alkyl electrophiles with secondary and tertiary alkyl Grignard reagents. The method is distinguished by its broad substrate scope and high functional group tolerance. Copyright

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.

Design and Development of New Chemical Reactions via Low-valent Titanium-induced Cleavage of Carbon - Heteroatom Bonds

Low-valent titanium (LVT)-induced regioselective cleavage of N-arylmethyl bonds in preference to N-alkyl/aryl counterparts in N-arylmethylamines has been examined in detail and culminated in the design and development of new reactions, viz. novel approach to deprotection of N-benzylamines, reductive deoxygenation of carbonyls to methylenes and reductive amination of carbonyls under neutral conditions - all involving a known bonding change, viz. the directed cleavage of C-N bonds via LVT-mediated reactions.

SYNTHESIS AND CONVERSIONS OF METALLOCYCLES. 7. A NOVEL APPROACH TO THE SYNTHESIS OF 3,4-DIALKYL-SUBSTITUTED ALUMINACYCLOPENTANES IN THE PRESENCE OF Cp2ZrCl2

A novel approach was developed for the stereoselective synthesis of trans-3,4-dialkyl-substituted aluminacyclopentanes from α-olefins, metallic magnesium, and EtAlCl2 in the presence of catalytic amounts of Cp2ZrCl2.The hydrolysis and deuterolysis products of the 3,4-dialkyl-substituted aluminacyclopentanes obtained are only in the trans configuration.

Syntheses of (+/-)-Deoxyschizandrin and the Lignan, 1,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

(+/-)-Deoxyschizandrin (1) has been synthesised through a dimerisation reaction as a key step.The Grignard reagent from 1-(3,4,5-trimethoxyphenyl)-2-bromopropane (10) on reaction with 2-t-butyl-3-phenyloxaziridine gives 1,4-bis(3,4,5-trimethoxyphenyl)-2,3-dimethylbutane (11), which is cyclised using vanadium oxytrifluoride to get deoxyschizandrin (1).Following the above methodology, 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane (2), a lignan has also been prepared.

Electrochemical Reduction and Oxidation of Allenes

The allenes 1 - 3 are reduced on mercury at -2.17 V (sce) (1), -3.12 V (2), and below -3.30 V (3); they are oxidized on glassy carbon at 1.25, 1.65 V (1), 1.75 V (2), and above 2.25 V (3).In the preparative reduction 1 forms, depending on the workup, 86percent of 1,1,3,3-tetraphenyl-1-propene (6a) or up to 50percent of aldehyde 9, a formylation product of the rearranged radical anion intermediate; on carboxylation of the electrolyte 54percent of carboxylic acid 8 are formed.The allene 2 is hydrogenenated to give 30 percent of (E)-1-phenyl-1-propene (10) and hydrodimerized to form 30percent of yield s in methylene dichloride/methanol 61 - 73percent of 2-chloro-1,1,3-triphenylidene (13), which is probably formed by chlorine, that is electrochemically generated from methylene chloride.In methanol/dioxane 13 is not obtained but 71percent of indanone 16 are produced.The oxidation of 2 and 3 is unselective; due to follow-up oxidations many products are formed in low yield.

SYNTHESIS OF A LIGNAN SKELETON VIA NICKEL- AND PALLADIUM-PHOSPHINE COMPLEX CATALYZED GRINGARD COUPLING REACTION OF HALOTHIOPHENES

A lignan skeleton is prepared in good yield through desulfurization of 3,4-dibenzylthiophene or 2,5-diaryl-3,4-dimethylthiophenes which are obtained by nickel- or palladium-phosphine complex catalyzed Gringard cross-coupling reaction of halothiophenes.