20264-89-5

Usage

Type of compound

Nitro-substituted butadiene derivative

Structure

Butadiene backbone with a nitrophenyl group attached

Usage

Organic synthesis and chemical research as a starting material

Applications

Pharmaceutical and agricultural industries, production of specialty chemicals

Suitability

Photochemical reactions and building block for new chemical structures

Safety

Hazardous if not properly managed, requires caution during handling and use

Upstream product

• 1734-79-8 3-(4-nitrophenyl)-2-propenal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1560-54-9 allyltriphenylphosphonium bromide 
• 555-16-8 4-nitrobenzaldehdye 
• 918540-63-3 4-(4-nitrophenyl)-3-buten-2-ol 

Downstream Products

• 1198351-40-4 N-phenyl-2-(4-nitrophenyl)pyrrole 
• 49678-08-2 3-(4-nitrophenyl)-propenal 
• 1394249-63-8 3-{(Z)-[(2S)-2-(4-nitrophenyl)cyclohex-3-en-1-ylidene]methyl}-1,3-oxazolidin-2-one 
• 107558-41-8 (+/-)-3c-(4-nitro-phenyl)-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride 

Relevant academic research and scientific papers

Catalytic (3+2) Palladium-Aminoallyl Cycloaddition with Conjugated Dienes

We describe the design and application of tailored aminoallyl precursors for catalytic (3+2) cycloaddition with conjugated dienes via a Pd-aminoallyl intermediate. The new cycloaddition reactions override the conventional (4+3) selectivity of aminoallyl cation cycloaddition through a sequence of Pd-allyl transfer and ring closure. A variety of highly substituted or fused pyrrolidine rings were synthesized using the cycloaddition, and can further undergo [1,3] N-to-C rearrangement to five-membered carbocycles with a different palladium catalyst. The utility of the (3+2) cycloaddition is also demonstrated by the preparation of various derivatives from the bicyclic pyrrolidine products.

Copper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines

Highly-functionalized pyrroles could be effectively synthesized from 3,6-dihydro-1,2-oxazines using a heterogeneous copper on carbon (Cu/C) under neat heating conditions. Furthermore, the in situ formation of 3,6-dihydro-1,2-oxazines via the hetero Diels-Alder reaction between nitroso dienophiles and 1,3-dienes and the following Cu/C-catalyzed pyrrole synthesis also provided the corresponding pyrrole derivatives in a one-pot manner.

Gas-phase pyrolytic reaction of 4-Aryl-3-buten-2-ols and allyl benzyl ethers: Kinetic and mechanistic study

Flash vacuum pyrolysis (FVP) of 4-aryl-3-buten-2-ols [ArCH=CHCH(CHs)OH, where Ar is phenyl, p-MeO, p-Me, p-Cl, p-NO2] gave the corresponding buta-1,3-dien-1-ylbenzene (ArCH=CH-CH=CH2, where Ar is Ph, p-MeO, p-Me, p-Cl, pNO2) and 7-×-1,2-dihydronaphthalene derivatives (where X is H, MeO); FVP of 1-aryl-3benzyloxyl-1-butenes and benzyl cinnamyl ethers [ArCH=CHCH(X)OCH2Ph, where Ar is phenyl, p-MeO, p-Me, p-Cl, X is H, Me, Ph] gave the corresponding but-2-en-l-ylbenzene derivatives (ArCH 2CH=CH-X, where X is H, Me, Ph) together with benzaldehyde. The proposed mechanism of these pyrolytic transformations was supported by kinetic and product analysis.

Trapping reactive metal-carbene complexes by a bis-pocket porphyrin: X-ray crystal structures of Ru=CHCO2et and trans-[Ru(CHR)(CO)] species and highly selective carbenoid transfer reaction

What's in my pockets? By employing Suslick's bis-pocket porphyrin (ttppp), a reactive M=CHCO2Et complex and a trans-[M(CHR)(CO)] (M = Ru) complex have been structurally characterized by X-ray crystal analysis. The sterically encumbered ttppp ligand has a significant impact on both the diastereoselectivity and chemoselectivity in metalloporphyrin-catalyzed reactions of ethyl diazoacetate with conjugated aryl dienes.