1415237-87-4

Upstream product

• 6626-84-2 dimethyl 2-benzylidenepropanedioate 
• 100-52-7 benzaldehyde 
• 108-59-8 malonic acid dimethyl ester 
• 3709-20-4 dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate 
• 10544-50-0 sulfur 

Downstream Products

• 605-02-7 1-phenylnaphthalene 
• 30877-08-8 1,2-diphenylnaphthalene 
• 29304-63-0 2-methyl-1-phenylnaphthalene 
• 204530-94-9 1-(4-bromo-phenyl)-naphthalene 
• 27331-34-6 1-(4-methylphenyl)naphthalene 
• 101735-32-4 1-phenyl-2-ethylnaphthalene 
• 2765-23-3 1-(4-nitrophenyl)naphthalene 
• 27331-43-7 1-(3-methoxybiphenyl)naphthalene 
• 604-53-5 1,1'-bisnaphthalene 
• 78176-92-8 2-(naphthalen-1-yl)benzo[b]thiophene 

Relevant academic research and scientific papers

Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates

A method has been developed for the synthesis of substituted β-styrylmalonates by conversion of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) in the presence of gallium trichloride into the corresponding- 1,2-zwitterionic intermediates or (2-arylethyl-idene)malonates, followed by treatment with pyridine at room temperature leading to an isomerization of the emerging double bond. This method allows one to expand these reactions to include ACDCs with acceptor substituents at the aromatic ring.

"cyclopropanation of Cyclopropanes": GaCl3-Mediated Ionic Cyclopropanation of Donor-Acceptor Cyclopropanes with Diazo Esters as a Route to Tetrasubstituted Activated Cyclopropanes

A new ionic cyclopropanation process involving the addition of diazo esters to donor-acceptor cyclopropanes (DAC) activated by GaCl3 has been developed. The reactions occur via 1,2-zwitterionic gallium complexes with elimination of nitrogen in all cases to give 1,1,2,3-tetrasubstituted cyclopropanes as the main products. Also, a number of related processes with the formation of various polysubstituted cyclopropanes, alkenes, and cyclobutanes, including products of multiple diazo ester addition, have been developed. Obtained by the developed method tetrasubstituted cyclopropanes are activated cyclopropanes such as DAC and can be used for further synthesis in this capacity. Their new reaction with benzaldehyde promoted by TiCl4 and involving one of the additional functional groups has been demonstrated, which leads to five-membered lactones. The mechanisms of the occurring processes, as well as the structures and stereochemistry of a rich range of products formed, are discussed in detail.

Ionic Ga-Complexes of Alkylidene- And Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry

A new synthetic concept was suggested in the chemistry of substituted methylidenemalonates that enables their utilization as 1,2-zwitterionic synthons. This strategy is to generate liquid ionic Ga complexes from methylidenemalonates and GaHal3with a strict 3/4 composition and then use them in further synthesis. A number of complexes with different metal halides have been synthesized and studied in detail. The unique properties of gallium among all metals have been demonstrated and explained. On the basis of the discovered new class of gallium complexes of methylidenemalonates, a number of novel reactions with acetylenes have been elaborated, which are unknown in the conventional chemistry of methylidenemalonates. The main demonstrated process is a three-component addition to a triple bond involving halide anions, leading to the formation of polyfunctional vinyl halides with highE-selectivity. The mechanism has been studied experimentally in fine detail. Application of specially optimized71Ga NMR spectroscopy makes it possible to take an in-depth look into the gallium chemistry in a new light. In particular, the key participation of GaHal4-anions in the occurring transformations has been established.

GaCl3-Mediated Isomerization of Donor-Acceptor Cyclopropanes into (2-Arylalkylidene)malonates

A new process for isomerization of donor-acceptor cyclopropanes (2-arylcyclopropanedicarboxylates) by treatment with anhydrous gallium trichloride to give (2-arylalkylidene)malonates in high yields and with good selectivity has been developed. The reactio

Four-Membered Cycle Formation Challenge: GaCl3-Promoted Formal [2+2]-Cycloaddition of Donor–Acceptor Cyclopropanes to Bicyclobutylidene

The first selective process of formal [2+2]-cycloaddition of donor–acceptor cyclopropanes (DAC) to multiple C–C bonds to form a four-membered ring in the product has been developed. Bicyclobutylidene is used do demonstrate this reaction. The process is promoted by GaCl3 and occurs through generation of 1,2-zwitterionic intermediates. A carbocationic rearrangement occurs in the bicyclobutylidene moiety. It results in expansion of both cyclobutane rings into five-membered ones and formation of a [2.3.3]propellane skeleton in the final product.

GaCl3-Mediated "inverted" Formal [3 + 2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Allylic Systems

A new process of "inverted" formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes (DACs) to allylic systems to give polyfunctionalized cyclopentanes has been developed. Unlike the classical version of formal [3 + 2]-cycloaddition, a DAC acts in thi

[4 + 2] Annulation of Donor-Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity

A new process for the [4 + 2] annulation of donor-acceptor cyclopropanes with acetylenes under the effect of anhydrous GaCl3 using 1,2-zwitterion reactivity was elaborated. The reaction opens access to substituted dihydronaphthalenes, naphthalenes, and other fused carbocycles. The direction of the reaction can be efficiently controlled by temperature.

Complexes of donor-acceptor cyclopropanes with tin, titanium, and gallium chlorides - Mechanism studies

Hitherto unknown complexes of dimethyl cyclopropane-1,1-dicarboxylate with Lewis acids (Sn, Ti, and Ga chlorides) have been isolated and characterized. Their structures, which were previously assumed from theoretical considerations, have been confirmed, a