63405-68-5

Usage

Physical State

Colorless

Chemical Structure

The (E,E) configuration indicates that the double bonds are in the trans configuration.

Utility

Intermediate in the production of various chemicals
Utilized in organic synthesis

Reactivity

Reactive nature
Handled and used with caution due to potential for hazardous reactions

Upstream product

• 5695-63-6 1,3-dioxan-2-ylmethyl bromide 
• 623-27-8 terephthalaldehyde, 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 60075-78-7 3-(p-iodophenyl)-propanol 
• 624-38-4 para-diiodobenzene 

Downstream Products

• 130927-32-1 1,4-bis(3-hydroxy-1-(E)-propenyl)benzene 
• 153759-64-9 p-phenylene-3,3'-bis(allyl bromide) 

Relevant academic research and scientific papers

Stereoselective organocatalytic oxidation of alcohols to enals: A homologation method to prepare polyenes

A novel method for organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide range of aromatic and aliphatic substituted enals were successfully generated in high yields and exclusively stereoselective E-geometry. Moreover, varying the solvents and/or the loading amounts of IBX allowed for the selective oxidation of alcohols and aldehydes. Importantly, the homologous application of this method provided a selective and efficient way of preparing various highly sensitive conjugated polyene frameworks, which are enriched in natural products.

Chemoselective Heck arylation of acrolein diethyl acetal catalyzed by an oxime-derived palladacycle

A dimeric 4-hydroxyacetophenone oxime-derived palladacycle has been used as a very efficient precatalyst for the chemoselective arylation of acrolein diethyl acetal to give either cinnamaldehyde derivatives or 3-arylpropanoate esters by proper choice of the reaction conditions. The synthesis of cinnamaldehyde derivatives can be performed by Heck reaction of acrolein diethyl acetal with iodo-, bromo- or chloroarenes in N,N-dimethylacetamide (DMA) using K2CO3 as base at 120°C and tetra-n-butylammonium acetate (TBAA) and KCl as additives, followed by acid workup. In the case of 3-arylpropanoate esters the corresponding arylation of acrolein diethyl acetal with iodoarenes can be performed at 90°C in aqueous DMA using (dicylohexyl)methylamine as base, whereas for bromoarenes the reaction has to be performed at 120°C using tetra-n-butylammonium bromide (TBAB) as additive. Alternatively, this process can be performed under microwave irradiation. These couplings take place in good yields and with lower catalyst loading than with palladium(II) acetate as well as in shorter reaction times and with lower excess of acrolein diethyl acetal.

Preparation of all-trans-(1,4-Phenylenehexa-1,3,5-trienylene) Oligomers

All-trans-(1,4-phenylenehexa-1,3,5-trienylene) oligomers, all-trans-1,4-bis(6-phenylhexa-1,3,5-trienyl)benzene (PHT2) and all-trans-1,6-bishexa-1,3,5-triene (PHT3), were prepared respectively by the Wittig reaction from 1,4-phenylenediacrylaldehyde or 1,6-bishexa-1,3,5-triene.The (1)H NMR, IR and UV-VIS spectra of the crude oligomers indicated the presence of cis double bonds in the trienes.The cis-trans isomerization of these double bonds was carried out by heating the cis-containing crude product in an appropriate solvent with iodine catalysis.The structures of PHT2 and PHT3 were confirmed by comparison of their IR spectra with that of all-trans-1,6-diphenylhexa-1,3,5-triene.