1138-83-6

Basic information

• Product Name: Benzene, 1,1'-[(1Z)-1-propene-1,3-diyl]bis-
• CAS NO: 1138-83-6
• Molecular Formula: C15H14
• Molecular Weight: 194.276
• Mol File: 1138-83-6.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[(1Z)-1-propene-1,3-diyl]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[(1Z)-1-propene-1,3-diyl]bis-(1138-83-6)
• EPA Substance Registry System: Benzene, 1,1'-[(1Z)-1-propene-1,3-diyl]bis-(1138-83-6)

Safety Data

• Hazardous Substances Data: 1138-83-6(Hazardous Substances Data)

Upstream product

• 14097-24-6 1,3-diphenylpropan-1-ol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 3536-29-6 2,3-diphenyl-1-propanol 
• 22379-62-0 potassium benzyloxide 
• 122-78-1 phenylacetaldehyde 
• 59130-21-1 1,1-dichloro trans-2,3-diphenylcyclopropane 
• 864078-99-9 C₃₁H₃₆N₃P 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 105512-32-1 3-Methoxy-1-phenylthio-1-propene 
• 40145-79-7 1,2-diphenyldiazoethane 
• 100-52-7 benzaldehyde 
• 103-63-9 1-phenyl-2-bromoethane 
• 82294-45-9 Triphenyl-(2-phenyl-1-trimethylsilanyl-ethyl)-phosphonium; bromide 
• 64-19-7 acetic acid 

Downstream Products

• 62753-15-5 3-nitro-1,3-diphenyl-1-propene 
• 34862-96-9 3-bromro-1,3-diphenyl-1-propene 
• 100-52-7 benzaldehyde 
• 103-82-2 phenylacetic acid 
• 65-85-0 benzoic acid 
• 1083-30-3 dihydrochalcone 
• 1044264-32-5 2-carboethoxy-2-(1,3-diphenyl-2-propenyl)cyclopentan-1-one 
• 258881-76-4 2-[(2E)-1,3-diphenylprop-2-en-1-yl]-1,3-diphenylpropane-1,3-dione 
• 171927-27-8 3-[(2E)-1,3-diphenylprop-2-en-1-yl]-pentane-2,4-dione 
• 1070203-83-6 2-[(2E)-1,3-diphenylprop-2-en-1-yl]-1-phenylbutane-1,3-dione 
• 116118-03-7 (E)-(3-methoxyprop-1-ene-1,3-diyl)dibenzene 
• 87614-83-3 (E)-3-ethoxy-1, 3-diphenylprop-1-ene 
• 125206-15-7 phenyl styryl ketone ethylene acetal 

Relevant articles and documents

Copper-Catalysed Allylic Substitution Using 2,8,14,20-Tetrapentylresorcinarenyl-Substituted Imidazolium Salts

Unsymmetrical imidazolium salts, each having one nitrogen atom (N1) substituted by a cavity-shaped TPR group (TPR = 2,8,14,20-tetrapentylresorcinaren-5-yl), were tested in situ as proligands for the copper-catalysed allylic arylation of cinnamyl bromide w

N-Heterocyclic carbenes as ligands in palladium-catalyzed Tsuji-Trost allylic substitution

A Pd(0)-catalyzed allylic substitution (i.e., Tsuji-Trost reaction) using N-heterocyclic carbene as a ligand was investigated. It has been proven that an imidazolium salt 2d having bulky aromatic rings attached to the nitrogens in its imidazol-2-ylidene skeleton is suitable as a ligand precursor and that a Pd2dba3-imidazolium salt 2d-Cs2CO3 system is highly efficient for producing a Pd-NHC catalyst in this reaction. Allylic substitution using a Pd-NHC complex differed from that using a Pd-phosphine complex as follows: (1) the reaction using a Pd-NHC complex required elevated temperature (50 °C or reflux in THF), (2) allylic carbonates were inert to a Pd-NHC complex, and (3) nitrogen nucleophiles such as sulfonamide and amine did not react with allylic acetate. It was also found that allylic substitution with a soft nucleophile using a Pd-NHC catalyst proceeds via overall retention of configuration to give the product in a stereospecific manner, the stereochemical reaction course obviously being the same as that of the reaction using a Pd-phosphine complex.

Single-Step Synthesis of Dinuclear Neutral Gold(I) Complexes with Bridging Di(N-heterocyclic carbene) Ligands and Their Catalytic Performance in Cross Coupling Reactions and Alkyne Hydroamination

We report on a single-step procedure for the synthesis of dinuclear gold(I) complexes with bridging di(N-heterocyclic carbene) (diNHC) ligands of general formula Au2Br2L1-9 (L = diNHC). The obtained complexes differ in the bridging group between the carbene donors and in the terminal wingtip substituents at the imidazol-2-ylidene rings. The complexes have been characterized by means of elemental analysis, NMR spectroscopy, ESI-MS spectrometry, and single-crystal X-ray structure analysis. The dinuclear gold(I) complexes have been tested as homogeneous catalysts in technologically relevant reactions such as the cross coupling between phenylboronic acid and aryl bromides and the intermolecular hydroamination of alkynes. The catalytic performance has been compared for complexes Au2Br2L1-9 and the benchmark mononuclear complex IPrAuCl.

Asmic Isocyanide-Nitrile Isomerization-Alkylations

Anisylsulfanylmethylisocyanide, Asmic, is a versatile building block whose alkylations provide a range of substituted isocyanides. The anisylsulfanyl group plays a critical role in the sequenced deprotonation-alkylation and the subsequent sulfanyl-lithium exchange. Complexation of the anisylsulfanyl group to BuLi in the presence of TMEDA affords a lithiated isocyanide whose alkylations generate trisubstituted isocyanides. In the absence of TMEDA, BuLi triggers cyanide expulsion to afford a transient carbene; reorientation of cyanide with attack at the carbene affords a lithiated nitrile whose alkylations afford quaternary nitriles. The complexation-induced isocyanide-nitrile rearrangement is exceptionally facile, occurring within 5 min at –78 °C. Detailed mechanistic and computational analyses identify the importance of chelation in the bifurcating mechanism: internal chelation favors cyanide extrusion to form a carbene whereas chelating agents favor arylsulfanyl-lithium exchange to generate a lithiated isocyanide. The combined experimental and computational analyses reveal a new mechanism for isocyanide-nitrile isomerization which provides valuable insight for rapidly assembling substituted isocyanides.

Catalytic membrane-installed microchannel reactors for one-second allylic arylation

A variety of catalytic membranes of palladium-complexes with linear polymer ligands were prepared inside a microchannel reactor via coordinative and ionic molecular convolution to provide catalytic membrane-installed microdevices, which were applied to th

Samarium diiodide-induced couplings of carbonyl compounds with methoxyallene leading to 4-hydroxy 1-enol ethers

(Matrix presented) A surprising samarium diiodide-induced coupling reaction of carbonyl compounds with methoxyallene provided 4-hydroxy 1-enol ethers, which are versatile synthetic building blocks. In this coupling reaction, methoxyallene serves as an acrolein equivalent, which cannot directly be employed.

Anti Eliminations of Horner-Wittig Intermediates

Erythro phosphinyl alcohols 3 and the threo isomers 4 give (E)- and (Z)-alkenes, respectively, by an anti elimination in contrast to the syn Horner-Wittig elimination of the corresponding phosphinoyl alcohols.

Influences of Phenyl Rings on NHC Ligands with Bicyclic Architectures

In addition to phosphanes, olefins, amines, and amides, over the past two decades N-heterocyclic carbene (NHC) has emerged as a useful alternative ligand. Based on a number of derivatization studies on NHC ligands, imidazol-2-ylidene and imidazolin-2-ylidene became the standard heterocyclic form, and bulky substituents have commonly been introduced on the nitrogen(s) adjacent to carbenic carbons. Our group previously developed NHCs equipped with noncarbenic carbons with a bicyclic architecture that gives them unique steric properties that make them bulky but accessible. In this study, we synthesized a novel type of NHC ligand that possesses a bicyclo[2.2.1]heptane architecture, and we compared five derivatives using copper-catalyzed allylic arylations with aryl Grignard reagents. The regioselectivity of the substitution obviously indicates that a phenyl ring over an active site has a characteristic effect on the resultant copper catalysts when γ-substitution is the major pathway.

Gold(I)-assisted α-allylation of enals and enones with alcohols

The intermolecular α-allylation of enals and enones occurs by the condensation of variously substituted allenamides with allylic alcohols. Cooperative catalysis by [Au(ItBu)NTf2] and AgNTf2 enables the synthesis of a range of densely functionalized α-allylated enals, enones, and acyl silanes in good yield under mild reaction conditions. DFT calculations support the role of an α-gold(I) enal/enone as the active nucleophilic species. A golden ally in allylation: In a gold(I)-assisted formal α-allylation of acrylaldehyde, enones, and acyl silanes with alcohols, allenamides were used as precursors to intermediate α-gold-substituted unsaturated carbonyl compounds. The transformation enabled the synthesis of a diverse range of products under mild conditions (see scheme; ItBu=1,3-di(tert-butyl)imidazol-2-ylidene).

Palladium/Phosphinated Polystyrene as a Catalyst in the Heck Arylation. A Comparative Study

Palladium anchored to phosphinated polystyrene with a Pd/P ratio of 1/1 gives very high activity in the arylation of methyl acrylate and styrene with iodobenzene.A comparative study shows that this catalyst is considerably more efficient than Pd/C, Pd(OAc)2, PdCl2, Pd(OAc)2/2PPh3, or Pd(PPh3)4.ESCA and X-ray studies have been used to determine that the active state of the catalyst is metallic palladium.This is further supported by a study of the product distribution of two reactions that are very sensitive to the type of catalyst employed, namely, the arylation of butyl vinyl ether and trimethylallylsilane, as well as by the fact that iodo- but not bromobenzene reacts with this catalyst.The polymer-bound catalyst with a Pd/P ratio of 1/5 was unable to bring about any arylation starting from iodobenzene, after 3 h.During the same time the catalyst with a ratio Pd/P of 1/1 gave full conversion.Nevertheless the former catalyst resulted in the highest activity when bromobenzene was used as the reagent.This suggests that a comparatively stable palladium (0) phosphine complex is the reacting species in this special case.Addition of triphenylphosphine to Pd/C gives, in contrast to plain Pd/C, a similar product pattern as Pd(OAc)2/2PPh3 on arylation of butyl vinyl ether and trimethylallylsilane, respectively.