78173-73-6

Basic information

• Product Name: diethyl (Z)-2-benzylidenesuccinate
• Synonyms: diethyl (Z)-2-benzylidenesuccinate
• CAS NO: 78173-73-6
• Molecular Weight: 262.306
• Mol File: 78173-73-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: diethyl (Z)-2-benzylidenesuccinate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (Z)-2-benzylidenesuccinate(78173-73-6)
• EPA Substance Registry System: diethyl (Z)-2-benzylidenesuccinate(78173-73-6)

Safety Data

• Hazardous Substances Data: 78173-73-6(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 2409-52-1 diethylitaconate 
• 100-52-7 benzaldehyde 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 1520-50-9 but-2-enedioic acid diethyl ester 
• 141-05-9 Diethyl maleate 
• 78173-74-7 C₂₆H₂₆O₄P^(1-) 
• 23360-63-6 triphenyl-(α-carbethoxy-β-carboxyethyl)phosphonium betaine 
• 78173-56-5 2-Benzyl-3-(triphenyl-λ⁵-phosphanylidene)-succinic acid diethyl ester 

Downstream Products

• 21307-94-8 diethyl (2R)-2-benzylsuccinate 
• 21307-94-8 diethyl (S)-2-benzylsuccinate 
• 21654-18-2 1,4-diethyl 2-benzylsuccinate 

Relevant articles and documents

Phosphine-Catalyzed Reaction between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction

A series of 1,2-dihydroquinolines were synthesized in good to excellent yields by reacting 2-aminobenzaldehyde derivatives and dialkyl acetylenedicarboxylates with catalytic amounts of phosphine. This reaction was rendered catalytic by the selective in situ phosphine oxide reduction with the use of phenylsilane. Furthermore, with the same starting materials and with an additional role of the reducing agent, a new olefination reaction was discovered. Hydrogen/deuterium (H/D) exchange experiments revealed the possible mechanism of this reaction.

First Base-Free Catalytic Wittig Reaction

The first base-free catalytic Wittig reaction utilizing readily available Bu3P (5 mol %) as an organocatalyst is reported. The initial Michael addition of the phosphine to a suitable acceptor substituted alkene ultimately results in the formation of an ylide which is subsequently converted with an aldehyde. The presented 1H NMR studies actually reveal evidence for the Michael addition and proposed ylide formation. Under the optimized reaction conditions various maleates and fumarates were converted with aromatic, heteroaromatic, and aliphatic aldehydes to evaluate the scope and limitations of this unprecedented reaction. Notably, maleates and fumarates react in a stereoconvergent fashion. The corresponding products were obtained in up to 95% isolated yield and E/Z-selectivities up to 99:1.

Pd(II)-Schiff base complexes heterogenised on MCM-41 and delaminated zeolites as efficient and recyclable catalysts for the heck reaction

We present a widely applicable approach for the preparation of Pd-complexes supported on silica-based mesoporous and laminar inorganic solids (silica gel, purely siliceous and acidic MCM-41, and delaminated zeolites ITQ-2 and ITQ-6) which involves the use of the Schiff bases 2-tert-butyl-4-methyl-6{(E)-[(2S)-1- (1-arylmethyl)pyrrolidinyl]imino}methylphenol (aryl = phenyl, 1-naphthyl, 2-naphthyl) as anchored ligands. As an extension of our research in recyclable catalytic systems we report results demonstrating the reactivity and recyclability of these systems for the Heck reaction (in a biphasic mode using ethylene glycol and toluene) and Suzuki coupling under phosphine-free conditions. The complexes are insensitive to oxygen or moisture, and no change of their activity was observed when exposed to an open system during the usual operation. No palladium black was observed after an extended reaction time and no residual palladium was detected from the filtrate at the end of the reaction.