70178-90-4

Basic information

• Product Name: Benzene, (1-ethenyl-1-propenyl)-, (E)-
• CAS NO: 70178-90-4
• Molecular Formula: C11H12
• Molecular Weight: 144.216
• Mol File: 70178-90-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzene, (1-ethenyl-1-propenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (1-ethenyl-1-propenyl)-, (E)-(70178-90-4)
• EPA Substance Registry System: Benzene, (1-ethenyl-1-propenyl)-, (E)-(70178-90-4)

Safety Data

• Hazardous Substances Data: 70178-90-4(Hazardous Substances Data)

Upstream product

• 74752-47-9 4-(2-butenyl)-2-phenyl-1,3,4-oxadiazolin-5-one 
• 64035-02-5 (Z)-penta-1,3-dien-3-ylbenzene 
• 89228-82-0 phosphoric acid diethyl ester 2,3-pentadienyl ester 
• 114419-86-2 4-methyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol 
• 65032-23-7 penta-2,3-dien-1-ol 
• 10409-50-4 phosphoric acid diethyl ester 1-phenyl-propenyl ester 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 64035-02-5 (Z)-penta-1,3-dien-3-ylbenzene 

Relevant articles and documents

A General Nickel-Catalyzed Kumada Vinylation for the Preparation of 2-Substituted 1,3-Dienes

The identification of two nickel(II) precatalysts for the preparation of 2-substituted 1,3-dienes by a Kumada cross-coupling between vinyl magnesium bromide and vinyl phosphates is described. This is noteworthy as engaging only one vinyl derivative in a transition-metal-catalyzed cross-coupling reaction is already reputedly challenging. Salient features of this method are its operational simplicity, the mild reaction conditions, the low catalyst loadings, the short reaction times, its scalability, and the use of stoichiometric quantities of each coupling partner. The tolerance of the two nickel catalysts to an important number of reactive functional groups and their compatibility with structurally complex molecular architectures has been extensively delineated. A Negishi variant of the reaction has been developed for even more sensitive organic functions such as ester or nitrile. Several other conjugated 1,3-dienes with various substitution patterns have been prepared by combining commercial alkenyl Grignard reagents and/or readily available alkenyl enol phosphates. Proper choice of the nickel catalyst and the reaction temperature gave access to a variety of different olefin isomers with high levels of stereocontrol. Overall, this approach affords conjugated dienes that would not be accessible otherwise and therefore provides a valuable complement to existing methods.

SYNTHESE STEREOSELECTIVE DE DIENES CONJUGUES A PARTIR D'ALCOOLS α-ALLENIQUES

The reaction of a Grignard reagent with an α-allenic phosphate leads exclusively in every studied case to 1,3-dienes.A high stereoselectivity is observed for the formation of both double bonds; particularly, the organometallic species attacks preferentially in a trans direction from a group located on the terminal allenic carbon.In the case of the esters of secondary alcohols, it is more difficult to determine the factors which govern the stereochemistry of the other double bond.The Z configuration is then favoured in the reaction phosphate + RMgX but the E configuration is predominant in the reaction acetate + R2CuLi.